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Question #129: “I am the Mayor of the Friend Zone.”

A still image from a SuperMario game where Mario is trying to jump from the Friend Zone to the (much higher) Relationship Zone.

COMMENTS ON THIS POST ARE NOW CLOSED.

There’s no way to turn off comments to individual posts, so we’re on the honor system here as of Friday, 3:45 pm CDT.

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Hello, Awkward Nation.

I get many versions of the question “How do I get better at meeting & dating women/men?” in the Captain Awkward Mailbag.

The answer is always some combination of:

  • Work on your social skills in general.
  • Dating is a crapshoot! For many geeks people that is incredibly stressful, because we like rules and being good at stuff. Give us the cheat codes! Tell us how to be good at stuff!  SORRY. IT IS TOTALLY SUBJECTIVE AND UNFAIR.
  • Your best chance is to throw out the weird sexist rules and expectations that you’ve inherited from romantic comedies, shiny magazines, beer commercials, and dipshits.  To quote Holly, “if you follow Cosmo’s advice, your dating life is going to be like trying to get asked to slow dance at the seventh grade socialforever.”
  • When in doubt, use your words.  Don’t infer; ask.  Don’t hint; say.

Fortunately, we have Intern Paul to answer today’s version of this question, and he can totally do it without a rantlecture about Jean-Luc Godard’s sexist portrayal of women as cruel childlike aliens who can never be understood (only desired) vs. Agnes Varda’s exploration of ambivalence or Vera Chytilova’s spectacular depiction of feminist rebellion as destructive play. Ahem.

Dear Captain Awkward:

I have a problem. It feels like whenever I meet someone I like and want to date, they like me back, but just as friends. I don’t mean that they tell me that as a polite way of turning me down, I mean that they are sincerely interested in striking up a relationship with me, but one that is completely platonic. Much of the time, that’s what happens. In fact, I’ve only had one serious relationship in my life (over ten years ago), but I’ve made about a dozen friends by asking out women I was attracted to.

When I was younger, I’ll grant that I was something of a Nice Guy, at least in the sense that rather than trying to ask women out and see what happened, I would just be friends with them and hope they’d come around and fall for me (ie, I was the guy in the xkcd comic), but I learned pretty quickly all the reasons why that was a bad idea and I stopped. Even when I’m completely upfront from the start, I get the same reaction. I’ll meet someone, feel a spark, and ask her out, but then around either the first or second date, she’ll tell me that she really likes me and likes spending time with me, but only as friends. And no matter how I meet them–mutual friends, social events, online, at work, etc.–it’s no different. And I wouldn’t say that I have a type, either, so it’s not as if I’m only attracted to the sort of woman who wouldn’t be attracted to someone like me.

I can’t understand why this keeps happening. I’m not unattractive, and clearly pretty likable. If insanity is trying the same thing over and over and expecting a different result, then I need to do something different if I want to actually attract someone. But I like who I am, and I’m satisfied with how I look, so I don’t know what I could or should be doing differently.

Sincerely,
The Mayor of the Zone

Dear Mr. Mayor,

Reading your letter reminds me of another letter that recently appeared here in my basement cubicle at Captain Awkward Dot Com Enterprises:

Dear Intern Paul,

I have a problem. I am the head coach of a professional football team in Florida and no matter what I do we can’t seem to win a game. My offense doesn’t know how to score and my defense has yet to learn the art of no. Things have gotten really uncomfortable at work and I think I’m in danger of losing my job. I don’t understand why this keeps happening, what can I be doing differently?

Sincerely,
Mustached in Miami

Although you guys are asking the same questions, it’s much easier for me to answer Tony…er…Mustached’s question than yours because I’ve seen tapes of his games and can cite statistics showing where his problem areas are. Unfortunately we have no such things to fall back on when it comes to your dates*. Clearly something ain’t working, but who knows what.

*Although we TOTALLY SHOULD have that! Anyone want to start SADR (the Society for American Dating Research) with me and keep track of arcane stats like AP (Awkward Pauses), TUFS (Time Until First Sexual entendre), and BEMM (Bitter Ex Mentions per Minute)? We’ll crack this dating nut yet. “Analysis shows a high correlation between a low TUFS and the total number of AP during a date! Don’t forget to try and keep your BEMM rate down!”

Like moths to a flame.

So I don’t know what to tell you. I think the first thing you need to examine is do these women really want to be friends with you, or were they just trying to let you down easy? Do you still hang out with them? Doing actual friend things? If so, I would take heart, at least you’re not completely turning these women off from you as a person.

How many dates are we talking here? 10? 20? Maybe they all had different reasons for why they didn’t see you as a match, none of which are “bad” things that are “your fault.” She likes Cool Wave but you smell like Arctic Ice. She’s Horde but you’re Alliance. She thinks leggings should count as pants and you don’t. She’s been having some very promising texts with an ex that’s she’s still into, but not anything big enough to just cancel on you.

I dated like a madman over this past summer, and none of those things got past a second date. None of the women were awful or unattractive or unlikeable, we just weren’t a good fit. Like a pair of pants that look fine but just aren’t the ones for you. All of the endings were for different reasons that probably speak to my own idiosyncrasies and might sound asinine to anyone else.* And I’m sure those women had their own problems with me. It’s not like they were ringing my phone off the hook looking to get together again! It’s all just bad fits and bad timing. The only way to overcome it is to date more women.

*One date argued in favor of perpetual indefinite copyright** “because otherwise companies might go out of business.” Also she did not understand what Civilization was and I had to explain it on several different levels. And she shook my hand at the end of Date #2. And she was from Wisconsin. See, bad fit. We did eat at a really good Vietnamese place, though.

**Yes I talk about copyright law on the second date. That’s why I get so much play.

Ill-fitting pants!

That being said, maybe you do have a problem. There could be something wrong with your approach and you might not know it. Maybe ask one of your dates-turned-friends for an honest assessment of why they weren’t interested in taking it further? Yeah, that does sound awkward and you’ll have to make the asking as non-creepy as possible, but maybe they can tell you something of value. Perhaps an email or text to your latest unfortunate fizzle, coupled with the promise that you’re just looking for data and will leave her alone whether or not she responds. One of my Summer Girls* did that with me and I tried to help her as much as I could.

*Lord, I fucking hate that song

In my consultations with The Captain, she suggested that you might want to give Craigslist Casual Encounters a try to see how your mojo works when you’re looking explicitly for sex rather than dating. In my experience, casual sex forges a kind of weird intimacy – you’re naked and vulnerable, and you have no baggage with the person you are with, so it’s almost like people give themselves permission to be more free and true with who they are. It might allow you to gain more insight into yourself, or give you a completely neutral observer to bounce things off of.

While I am the president of the Everyone Should Be A Happy Slut club, I’m not entirely convinced that CL is a great idea. If you’re having a tough time dealing with being ignored/rejected as a guy, CL ain’t going to make you feel better. There are lots and lots of men on there, and relatively few women. Even if you’re only replying to w4m ads that you think are likely to be real (and not spam or hookers, so that eliminates like 85% of the ads right there), the response rate is like ~3% and the “conversion rate,” if you will, is lower than that. So you’re already looking at tons more rejection.

You do have a much better chance if you write a good m4w ad for yourself. Differentiate yourself from the crowd by being intelligent and confident, clearly expressing what you want, and conveying that you are a safe and courteous sex partner (you are those things, right?). Also no penis photos.

I wish I could write up a magic gameplan that teaches you how to ask any lady out on a date and you’re givin’ each other the business in no time, but I can’t. That thing doesn’t actually exist. Women are just people, and like all other kinds of people they like all kinds of different things. So in the end you just have to keep trying until you find the woman that’s into your thing. Until then, be interesting, be caring, be respectful, and treat your dates the way you expect to be treated.

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COMMENTS ON THIS POST ARE NOW CLOSED. THANK YOU.  I will delete comments received after 3:45 pm CDT, Friday Nov. 4.

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74 comments
  1. Directed said:

    “If insanity is trying the same thing over and over and expecting a different result”

    Insanity is the presence of a mental illness…sometimes doing the same thing over and over and expecting a different result is the thing to do, if it is as you depict it and your problem is how you are meeting women and not what happens on the dates. Meeting women and asking them out, then going on dates and letting them decide where it goes is definitely the thing you’d want to keep doing.

    Aside from the Wisconsin comment (I am from Wisconsin, and I disagree with indefinite copyright and love Civilization!) this is exceptionally solid advise.

    • The Guy Who Wrote the Letter said:

      Here’s the thing, for me, dating isn’t a crapshoot. In craps, you occasionally win. I feel like the approach I’ve been taking to dating is really the approach I should be taking to make friends, because that is what it’s really effective at. On the other hand, it’s very ineffective at finding people who want anything more than friendship, so it’s hard to have faith that continuing on this path will work. That’s what I was getting at with the aphorism about insanity.

      One piece of feedback I have heard from one of the friends that I was interested in was that I don’t flirt. That does seem like it’s on the right track, because another issue that I’ve encountered is that sometimes when I ask women out, they’ll respond with something like “it sounds like you might be asking me out, and if that’s true, then I want to be clear that I only see you as a friend, but I might be way off base, so I’m sorry for being weird and presumptuous”. That or they’ll be surprised that I’m straight (that’s happened two or three times). Those encounters, plus my friend’s comment, lead me to think that a significant factor is that I’m bad at conveying to women my sexual interest in them.

      The issue I have with that, is that when I’m interacting with someone I’m interested in, I’m usually too engaged with the conversation to be thinking about how much I want to sleep with them. On the occasions when my sexual desire to them is more on the forefront of my mind, I don’t know how to express that without being crude. For example, I was recently on a date with a woman who happened to have impressive cleavage that would catch my attention from time to time. If I were to put into words the thoughts they inspired, it would be something like, “she has nice boobs; I hope this date goes well so I can see her naked later.” I can’t exactly say that. Or can I? Maybe I have this all wrong. I was just given to understand that that sort of thing is objectifying and demeaning, particularly during a substantive conversation.

      If that’s not an appropriate thing to say, but it is an acceptable thing to attempt to convey non-verbally, I have no idea how to do it. And even if I did know how to, I feel like that in order to do it, I would have to divert my attention away from the conversation, which seems objectifying and disrespectful. Most of the time though, it wouldn’t come up anyway, because I’m too engaged in the conversation for it to be on my mind.

      • I mean… flirting is just like having a conversation. You listen/watch for cues. You speak/act. You listen/watch for responses. I too get really involved in verbal conversations, and I often don’t notice when someone is flirting with me until he touches me, like a hand on my back or arm. It’s usually kind of awkward, and if I’m not into it I move away or ask not to be touched, and if I’m into it I’ll touch back or come right out and ask if he’d like to kiss me. When I’m the one initiating flirting, I rather ask first than randomly touch (unless we’re already randomly touching, like knees rubbing together). Or I’ll offer a true compliment – something more socially acceptable than “nice boobs” – and see what happens.

        There is a LOT of middle ground between friend zone and “nice boobs.” And you can definitely initiate and read cues in flirting in the same way you listen to a conversation. What you can’t do is know ahead of time what the outcome will be, or direct outcomes.

      • Directed said:

        I’m going to guess that there’s something much bigger going on than, “I don’t flirt.”

        Maybe the fact that you’re approaching dating like a game you can win or lose at. I definitely wouldn’t be into that, if we were on a date and I got that feeling. Or that you’re treating conversation as something that you have to do to hopefully get sex later. Do you want a date, or do you want sex? If someone is out with you thinking they’re dating, and you’re considering it a job interview for intercourse, you’re probably both going to end it unhappily.

        It also sounds like you’re having an issue with communication. If you’re saying, “Do you want to get coffee?” that might be why women are assuming it’s a friend thing. “Do you want to go out with me/go on a date?” is going to clear that up. You can make your intentions clear without being a creep. And, of course, always take no for an answer!

        • The Guy Who Wrote the Letter said:

          My rule of thumb for whether I ask someone out is whether I think we can sustain an interesting conversation for at least two hours, so I’m looking for good company on a date.

          I usually say “Do you want to go out this weekend” or something like that. I’m pretty careful about including the phrase “go out”, but it’s apparently not always heard or interpreted correctly.

          • dustyrose said:

            Maybe try “Do you want to go on a date this weekend?” I’m usually too much of a wimp to be that direct, but it might work for you.

          • k said:

            I agree with dustyrose. Be more obvious about it, because “go out” means go knock back a few cold ones and play some extremely platonic foosball in my world. Be like, “Do you want to go on a date with me. I am interested in dating you. On a date. A date, which is a date, as in DATE”

      • commanderlogic said:

        I don’t flirt…when I’m interacting with someone I’m interested in, I’m usually too engaged with the conversation to be thinking about how much I want to sleep with them.”

        10-4, good buddy. Whatever you think flirting is, please, PLEASE don’t do it. You’re doing fine. Interesting conversation IS flirting, or at least, it’s flirting the right way with the right people.

        “it sounds like you might be asking me out, and if that’s true, then I want to be clear that I only see you as a friend, but I might be way off base, so I’m sorry for being weird and presumptuous”.

        This tells me that you are not being direct when you ask the ladies on dates, and also, that there is some lead time before you summon up the courage to ask them out.

        Be direct, and be direct FAST, before you invest all your energy in some fantasy relationship that doesn’t actually exist. “Hey, are you doing anything [Date/time] because I’d like to take you to [event/dinner/combination].” Sound like a date? Because it is. Fully own it. There is no ambiguity of “maybe he wants to be my friend!” Ask her out, then if she says “no” you have no ambiguity, and can be cool with rejection, and maybe she has a friend who would like to be asked out.

        Good luck!

      • JenniferP said:

        Hey. Guy Who Wrote The Letter.

        I don’t want to steal Intern Paul’s thunder by writing you a whole new blog post in the comments (of my own blog), but it’s late and I am drinking a giant beer and feeling both introspective and also annoyed because I can see that you are probably not fun to date because you are a person who keeps asking the same question in slightly different ways. Want to know what’s probably sexier than your tedious example of trying to remain “respectfully and fully engaged in the conversation” while also surreptitiously admiring boobs and racking your brains for how you can convey that in a way that will Bloody Well Work This Time?

        Answer: Being so passionately and fully engaged in the conversation with this woman that it becomes an end in itself and you stop worrying about your next move or how respectful you appear, and letting the occasional flashes of glorious boobs in your peripheral vision be just…pleasant. Learn to live in the moment of “This conversation is super-interesting! She has beautiful breasts!” rather than the uncertain future where she will probably reject you like all those other women did in your imperfect past. Trust that a few moments from now it will be the right moment to say “I’ve loved talking with you so much, do you want to grab a drink somewhere quieter?” or “I think I have a copy of that book at my place, can I make you some tea and we can talk some more?” and that if she’s into you it will all flow from there.

        Learning to be fully present with people and stop trying to influence the outcome might be your one shot at sorting this out, and even then it’s still mostly up to chance.

        Here’s everything I know about finding love, starting with the givens:

        A) I am a prickly, picky, weird, introverted, standoffish, sarcastic, skeptical, bossy, pedantic, cynical, broke, depressed, late-blooming nerd.
        B) If I had to pick a celebrity I most resemble, it would be Lauren from Glee, who I would describe as “fabulous, but decidedly not for everyone.”
        C) When I say “picky”, I mean you must be at least as smart and funny as me to ride this ride, and you must be at least as cool as my friends and able to keep up. This limits my dating pool far more than the fatty-fat-fat thing does.
        D) If I think back on all of my major relationships – years-long, true-love connections! – the initial transition from “we are on a fun date now” to “holy sexual connection, Batman!” was fun and easy and happened within 1 or 2 dates. They were kind and smart and funny, I liked how they looked/smelled/sounded, and when we somehow managed to stop talking and bridge the physical space between us, it didn’t feel like work.

        Maybe they were all running some kind of fierce secret game on me just made it look effortless. More likely, somewhere in the universe the proverbial hundredth monkey on the hundredth typewriter accidentally typed Hamlet instead of kll;mlm;oim,.cx,mkljj;qweeqwjjnkfd!ww! and I met one of the several people among the 7 billion who I like who is also predisposed to like me. Impossible until it’s inevitable.

        In a struggle well-documented on this blog, I sort of managed to transform myself from being a creepy, overly-invested weirdo into a slightly cooler and more relaxed…eccentric person.

        To do this, I:

        -Met lots of people and went on lots of dates that didn’t work out.
        -Threw myself into career and artistic endeavors.
        -Worked on my own mental health issues.
        -Got older.
        -Realized that despite my awesome powers of persuasion, it is impossible to convince people they should love you by offering your own love as an (unasked for) sacrifice or by laying out a detailed and logical case or by mistaking really good sexual chemistry for more than it was.
        -Corollary to above: Decided to date only people who are as cool as my friends. I am deadly serious. On or after a first date, I literally ask myself, “Is this person as cool as Commander Logic? Will he have my back the way she does? Will he crack me up the way she does? Will he be loyal and fierce and witty and honest the way she is, and also understand about bacon and wine and cheese and *stories* and the joy of bad movies, watched in large groups?”

        That’s obviously a lot of pressure for a first date, especially since Commander Logic is just one of the brilliant, loyal, generous, talented, hilarious amazons (+ some dudes) that have my back. You people don’t even know. She’s like the shock troops of awesome who get you ready for when the awesome cavalry ride in on mighty steeds of Rohan and turn everything into victory and laughter.

        The first time I met Commander Logic it was at a Halloween party. I don’t even remember my own costume, but she had some awesome skull makeup on and looked gross and terrifying, and we talked for hours about books, and then I ran into her at ANOTHER Halloween party the very next night and she was wearing the same costume and we talked about books some more and not long after that we were FRIENDS. Boom.

        I’m telling you this because I think people make true friends the same way they make lovers – a little bit out of shared interests and proximity and a little bit out of a spark that makes you recognize that this is one of Your People. With a new friend, you should make an effort to get their email address or number and try to hang out! Sure you should look for signs of reciprocity and that they are actually as cool as they seem to be! Sure, you will sometimes wonder if they like you as much as you like them. But you don’t have *worry* about it. You don’t have to *strive* about it.

        Letter Writer, I feel like you are desperate to tease some kind of rubric or plan of action out of all of this, so I will try to give you one. Maybe when I say “Don’t date anyone who isn’t as cool as your friends” you’re looking around and seeing that your friends are all women who’ve rejected you and that’s not really helping you change it up. So.

        1. The next time you go out with a woman and you get the “Can we be friends?” thing say “Sure, maybe.”

        2. Remain pleasant and try to enjoy yourself, but extract yourself from the date as soon as politely possible.

        3. Be polite and pleasant if you happen to run into each other at social events. “Nice to see you! How are things?”

        4. Otherwise, never initiate contact with her again.

        Don’t be friends. Don’t pour effort into spending time and communicating with someone who has rejected you. Stop trying to figure out what you could have done differently. Stop trying to figure out what she wants. Don’t think about her. Don’t help her move. Don’t volunteer for her bake sale. Don’t go to her art show. Just walk away. Do that with the next one and the next one and the one after that. Do that forever until you find yourself in a cab or an elevator or on a couch or behind the shower curtain in the bathroom at a crowded party next to someone who is pointedly not looking at you while her hand snakes its way into yours and somewhere a monkey types the words “This above all: To thine own self be true.”

        That’s what I do with all the people who aren’t as cool as Commander Logic, et al.

        • Ahhh yes yes yes to the “Don’t be friends.” I never understand how people become surrounded by people they are sexually interested, because I rarely remain friends with exes or guys I’ve dated, howmsoever briefly. Not that they all end with such animosity that I never want to speak to them again, but unless there’s a reason to remain friendly (we work together, he’s always at that one coffee shop I like, he’s friends with my friend and I see him at parties, or we really do have good friend chemistry) that’s usually it for us. I have enough friends, male and female, as it is. I don’t need a parade of former lovers to bring that number up. And I think it’s okay, if you get told “I see us more as friends,” to respond with, “I appreciate that, but I am not looking for friendship at this point in my life, and I’m sorry we don’t have more of a connection.”

          Also, as long as we’re talking about being direct — Guy who wrote the letter — if you find yourself on a first or second date with a woman, and you find yourself occasionally checking out her loveliness and wishing to see more, pay her a physical compliment. Nothing creepy, but a simple, “You look lovely tonight” or “That top looks amazing on you.” Something like that that dispels the ambiguity — you find her attractive, you say so, she now has that information. Maybe she’ll rebuff you, or maybe she’ll respond in kind. I’m saying this as a lady who has had many deep and interesting conversations with men I’ve just met who I later found out were trying to flirt with me. The ones I’ve ended up kissing-with-tongues are usually the ones who, at some point during those deep and interesting conversations, said something that made it clear they were attracted to me — and if I felt the same, yahtzee!

          Otherwise, you’re just looking at women and being the gentle, creepy tea-cup video guy that CA has put up here once or twice.

        • The Guy Who Wrote the Letter said:

          I think I was unclear in my comments. These “boob moments” are fleeting; 98% of the time, I am completely engaged and in the moment and having a pleasant conversation. My concern was that because I pay so little attention to my sexual attraction that I come off as sexless. I’m not in the moment thinking “she has nice boobs; pretend to pay attention so I can touch them later”, I’m paying attention in the moment and only fleetingly even noticing my own desire to touch her boobs.

          • I’m not clear on why you’re framing this as paying attention to “your sexual attraction.” If you’re paying (non-creepy) attention to the *person* you’re attracted to, you’re already doing okay. It’s not about what inside your very soul (or your very junk) but about how you interact with the other person.

        • Kathleen D. said:

          “B) If I had to pick a celebrity I most resemble, it would be Lauren from Glee, who I would describe as ‘fabulous, but decidedly not for everyone.'”

          You are?? Luxury!

          I am Liz Lemony, for better or worse.

          • JenniferP said:

            I suspect that Velma from Scooby Doo is a safe Halloween costume choice for a lot of the regular readers here. :)

      • sasha said:

        You need to break the habit of analyzing social situations while you are in them.

        This is essentially the same old, “be in the moment” advice that you’ve heard over and over again, and it may seem about as useful as saying “don’t think of pink elephants,” because if you go into a social situation with the idea at the forefront of your mind that you need to not overthink things, you’ve already overthought things.

        That said, it’s clear from your comment response that you’re doing this. For example, you have a substantive conversation with a girl you like and try to focus on the serious issues being discussed, but you also notice what she looks like and try to plan out how you can slip in a compliment on her appearance without being too forward or disrespectful. You’re so worried about playing it wrong and making her uncomfortable that despite the fact you’re fastidiously sticking to the topic at hand, she can tell something’s up, and the one thing you most want to avoid happens: she feels uncomfortable.

        Something that helped teach me how to be in the moment was taking an improv class. In an improv scene, your first instinct, since you understand that scenes are supposed to be funny, is to try to stockpile some clever one-liners you can pull out when it’s your turn to talk. After a class or two, you realize how poorly that works. Scenes are constantly evolving, and if you try to plan out your words ahead of time, they sound old and stale by the time you actually use them. It’s better to not plan ahead, just embrace the possibility that you’ll say something dumb, and say it anyway. Doing this means displaying some real emotional vulnerability, which I always found scary as hell, but improv taught me that it had a big payoff. If you are emotionally open, the audience sympathizes with you and wants you to succeed, so even if you’re not saying the most objectively funny things that could be said, you’ve created a positive energy in the room that ends up making the scene a success.

        I don’t want to be too much of an improv evangelist, because I suspect that I really lucked out with finding a good place to take classes, having an amazing teacher, and being in the right frame of mind to be receptive to the life lessons we were getting in class, so your mileage may vary. However, given how hard it is to come up with *any* concrete steps you can take to practice being in the scene, instead of analyzing it from the outside, it’s worth a try.

        • The Guy Who Wrote the Letter said:

          I don’t analyze social situations when I’m in them. I’m analyzing them now.

          My fear was that I end up as just friends because I interact in the moment in a way that is basically no different than a friend would interact.

          • JenniferP said:

            Guy Who Wrote The Letter:

            Go ask someone else.

            We don’t know.

            Either you are doing everything right, but you haven’t clicked with One of the Right People yet, or you are doing something wrong (that we can’t tell because we haven’t met you and we don’t what’s in the hearts of the women you’re meeting).

          • Christen said:

            You don’t have to learn to flirt or learn to like flirting. It’s not for everyone. It’s impossible for me to know what your friends mean when they say you didn’t flirt (because flirting can be a lot of different things). Maybe they mean you waited too long to express interest or maybe they mean even when you were ostensibly On a Date, you didn’t convey that you were that into them. Or they were being polite.

            I could probably write an entire blog post about how to flirt as a geek, but I think this commenter covered it really well (and I am totally adapting some of this advice to my approach to my own podcast). If you’re talking to someone and you have a fleeting thought that her breasts look really great, or that her new haircut is really flattering r that you love how animated she looks when she gets to talking about a particular subject, you can say something about it. If you are on something that is explicitly a date, you can definitely say, “Hey, I am listening to you but I admit, I’m a little distracted because you look really cute right now,” watching her reaction, and then either getting back to the subject at hand or continuing the flirt thread depending on what seems right. If she seems REALLY weirded out or offended, apologize and move back to whatever you were saying. Otherwise, just watch her body language and wait for her to reciprocate.

            If the actual sentence your brain forms is something less subtle and more crass, or just awkward like, “Um, that is a very, um, flattering top you are wearing?” that can be OK too. I’ve felt actual relief when a gentleman caller shifted the conversation in a decidedly less gentlemanly direction, like: “PHEW. I’m not the only one standing here thinking, ‘I’m really interested in what you’re saying but also kind of would like to make out with you a whole bunch and then finish this conversation in bed later after some really hot loud sex, or perhaps over brunch tomorrow?'”

            As the Captain says, Acknowledge the awkward. Letting a conversation get weird can be the best thing that ever happens to you. If it feels natural to you to casually touch a lady’s shoulder or hand while, say, making a point (I’m not normally touchy-feely, but when I’m in the testing-the-waters stage with a new prospect I will totally lightly tap his shoulder or arm in the middle of a conversation), do it.

            But there isn’t really a cheat code to flirting successfully either. It comes with confidence and a willingness to take even tiny risks. Anything that feels forced or weird to you is more likely to feel weird to her too. And getting rejected a lot by a lot of ladies you’d become friendly or comfortable with can wreak havoc on your mojo. Which brings us back to the recommendation that perhaps seeking out and getting some sex-for-sex’s-sake would be a Good Thing to boost your confidence right now.

          • JenniferP said:

            Well said!

            There’s also some fallacy going on here that having sexy pants-feelings and acknowledging them is somehow disrespectful to women, like, “Well, I was totally into our conversation about Foceault, but you ruined it when you told me I was pretty.” No.

            I also sense that the Guy Who Wrote The Letter is bad at inviting women over into his space or picking up on when they are inviting him to their places. Going to someone’s place to “watch a movie” or “listen to music” at night after an intense 3-hour conversation isn’t a guarantee of sexytimes, but between two consenting adults who are into each other, it sure serves as one hell of a pretext. My favorite example of is from college: A guy I vaguely knew from classes and I ran into each other at an event at a bar. He reintroduced himself to me with something like “I always had the biggest crush on you, but you would never talk to me!” (100 points for leading with romantic/sexual interest and blunt honesty) and we had a long, geeky, and intense conversation about mythology broken up by some dancing and hanging out with our respective friends.

            Jump ahead to 3:00 in the morning when we’re heading back to our respective dorms and I realize that I need to “check my mail” (in a mailbox that happens to be in his dorm). 100 points to me for being a full human being with agency and desire who is not waiting for the other person to mysteriously and perfectly execute an arcane series of “moves.” Wait out the awkward interval when we have to walk down a long, dark, creepy hallway so I can actually check my mail. 100 points to him for saying something like “Well, now that you have your phone bill, howabout we watch a movie?” After this the point scale trends towards infinity.

            I am friends with that person decades later. We respect the ever-loving shit out of each other.

        • One very successful line that I did practice ahead of time was, “I’d really like to kiss you.” It’s not clever, but it’s honest and direct. And actually saying it to my date was incredibly difficult. But it broke the friend barrier.

      • Kathleen D. said:

        “…because another issue that I’ve encountered is that sometimes when I ask women out, they’ll respond with something like ‘it sounds like you might be asking me out, and if that’s true, then I want to be clear that I only see you as a friend, but I might be way off base, so I’m sorry for being weird and presumptuous’. That or they’ll be surprised that I’m straight (that’s happened two or three times). Those encounters, plus my friend’s comment, lead me to think that a significant factor is that I’m bad at conveying to women my sexual interest in them.”

        Oh. Actually, that sounds like you’re just fine at conveying your sexual interest in them, to them, they just aren’t returning it.

  2. karinacinerina said:

    Sorry, Directed – he was making a specific reference, not to mental illness, but the futility of not trying different approaches when hammering at the same approach that demonstrably doesn’t work: “Insanity: doing the same thing over and over again and expecting different results.” – a quote attributed to Albert Einstein.
    ANYWAY we’re all in agreement that this is excellent advice.

    I have had male friends who were the mayors of their own friendzones, and finally they just changed how they approached women – for example instead of being xkcd guy, he actually asked them out on a date right away, making his intentions known before they could decide on their own that it’s easier just to be friends. And he worked out and got super cuter too.
    I’d say LW is doing the right thing (being himself, not being all weird and insecure) but maybe needs to throw his nets wider. Either work those girl friends to meet their girl friends, or join all new social circles to widen the range of people he meets. I don’t mean ditch your friends, I mean take up a new hobby (dance classes, volunteering for things, organized sporting things) where you meet new people who don’t already have a predisposition to think of you as The Buddy.
    Best of luck!!!

  3. btothes said:

    All sound advice here. I wonder if football and dating have a little more in common than we thought? Again, without your playback tapes, we can’t see your game, but could it benefit a little injection of “clear eyes, full hearts, can’t lose,”? You like you, which is awesome, but maybe an experiment in turning up the mojo and belief you can turn the friend streak around might be all you need.

    My dating mantra lately has been “love it ’til you break it.” I ask the questions that come into my head, risk my poor heart and tell people why I think they are cool, and have found out boldness and sincerity work out. And if the dating isn’t working? You get to find out way sooner.

  4. tropical girl said:

    probably has to do with your physical demeanor. either you are invading personal space at a inappropriate times, or are not entering it at appropriate times. additionally, you may not be getting her cues about it. some guys just “know” when to touch a girl’s hand across the table, when to place an arm around her shoulder, etc., even in the early stages of dating. i’m not sure how one would learn these things, though, but perhaps start watching other people (real people, not movies) and being aware of it. also, it sounds like you have a rather subdued sex drive because you are actually thinking about the conversation rather than about sex. this can be a good thing, and i would recommend personal ads from women who enjoy things like “cuddling, long romantic walks, holdings hands, etc”. those women will surely appreciate that you will not just have sex occasionally but that you are patient and in control of the “brain down there” enough not to be jumping their bones all the friggin’ time!!! just some thoughts….

    • JenniferP said:

      Hello Tropical Girl! You may have nailed it – search for personal ads from women who indicate “I like to take it really slow.”

      Conversely, try to meet more slutty women who are comfortable making the first move.

      • I don’t think it’s fair to call women who make the first move ‘slutty’. I do that almost every time, and I know what I am: sexually aggressive. But, I am no ‘slut’- and no amount of Walking or ‘reclaiming’ will change the word from what it is- a misogynist insult. FTP.

        • JenniferP said:

          I’ve done All The Reading and I understand why you are mostly correct about that and maybe I’m having a “But I’m a vegan!” moment when I say: We use that word as a compliment around these parts.

          Result: I’m leaving your comment up for people to reflect on and possibly silently agree with you.

          Key word being “silently.” The “Can we use that word?” debates exist, ad absurdem, elsewhere on the internet. This is my house.

          Now, on the topic of the Letter Writer, probably his best possible romantic outcome is that a woman would like him and make the first move and he wouldn’t have to do anything to convince her. She will probably be very literal and direct, too. Which is to be absolutely encouraged.

  5. Yonmei said:

    I didn’t have a relationship with anyone for six years. I had a job that enthralled me, hobbies that pleased me, friends whose company I enjoyed, and a nice social life. I just never met anyone I liked, you know, in that way. And mostly this didn’t bother me: I like smart, funny, geeky lesbians who are tall enough and solid enough that I don’t have to stoop to look them in the eye and I don’t worry I’m going to break them when I hug them. There are not enough of those people around for me to spend a lot of time wishing they’d date me.

    Then I met a smart, funny, geeky lesbian who’s about an inch shorter than me (though we compete – depending on what boots we’re wearing, she’s sometimes taller than me) and she’s the same kind of build as I am and I think she’s great and she thinks I’m great, and, well, somewhere the Guardian Angel in charge of lesbian dating is heaving a sigh of relief as she scratches our two names off the waiting list.

    So you know, sometimes you just have to wait til you meet the right person. It’s not about whether you’re attractive or likeable. It’s just about whether you’ve found someone who thinks you’re totally delightful, even when you phrase the same question for the eighth time in a slightly different way, and you think she’s the eighth wonder of the universe even though she plays Horde and you’re Alliance. Or something.

  6. JB80 said:

    Hiya Captain and Intern Paul,
    I’m sorry if this comes across as a bit negative, but it sounds like the gist of your advice here is another variant of “just be yourself and wait until the Right One comes along”. Which is easy to say for those who are already in a relationship, but what about those for whom it just doesn’t seem to be happening? I know how the OP feels because I’ve been in his situation longer than I care to remember. I had no problem talking to girls and making girl friends, but never a girlfriend. And I didn’t know why, because nobody would tell me. I had my suspicions, but no way to confirm them.

    I wish I had a more concrete answer to give but I don’t. I don’t know why some people move from one relationship to another easily and effortlessly all their lives, while others seem doomed to be alone. It just seems unfair, shitty and frustrating. Meh, don’t mind me, it’s probably the wine talking.

    • JenniferP said:

      Sorry if this comes off as a bit negative, but:

      1. It is totally unfair and subjective. When it sucks, believe in the suck. It will suck until it doesn’t.

      2. I don’t know why people move “easily” from one relationship to another, while others have shitty and frustrating luck.

      3. I do know that what looks like “easily moving from one relationship to another” on the outside (when you are feeling alone and start thinking of all the worst people you know in the world who still manage to have a romantic partner) can actually consist of years-long dry spells or serially dating people who are not right for you and make you unhappy.

      The only advice I will ever have is: It will take time and it may not ever happen for you. What else are you doing with your life in the meantime? Work on getting really good at that and circle back to dating from time to time when you’re feeling awesome about other stuff. Whine as little as possible.

      I am single now. I didn’t plan to be or want to be. It pretty much feels like this. “Hi, I’m a walking time bomb of grief and regret, want to go out? May I offer you my shriveled, broken heart? Yes? You will love me, yes?” My plan is to focus on other stuff about my life, like becoming the World’s Greatest Film Director, until I achieve a pleasing numbness where the pain used to be.

      If you find that patronizing, go ask someone else. Intern Paul and I are not withholding the secret from you….the secret that we sell only to Super-Advanced-Premium Subscribers for many $$$$….or ARE we?

      • Jason said:

        Dear Beloved:

        I have been blessed with the Secret of Luv, and will share it with you. Please provide the name of your bank, and an account and routing number, and I will deposit the Secret of Luv in your checking account.

    • I don’t see the Captain as saying “wait for the Right One” at all. For one thing, the idea that there’s a Right One in the first place is putting a lot of heavy pressure on any given dating situation; I know it’s a persistent cultural fantasy we’ve all been trained in, but lots and lots of people fall in love multiple times over their lives, and it’s not because 99% were Fake Love and 1% was True Love. It’s because there’s such a thing as the Right Person at the Right Time. Captain’s advice is not “wait around and cross your fingers,” but more like “be engaging and direct and make an effort to meet people, and don’t force it because if you have to force it that’s probably not the Right Person at the Right Time.”

      I don’t know why some people move from one relationship to another easily and effortlessly all their lives, while others seem doomed to be alone.
      The thing about this is, while I totally get the emotion it comes from, the key word here is “seem.” Unless they’re your BFFs who tell you everything, you really don’t know anything about how easy or effortless a relationship is. You only know what people are letting you see, and then calling yourself “doomed” in comparison.

      In other words, there’s a huge difference between fate and luck. Fate is Doom and True Love and the Right One and Effortlessness; luck is the Right Person at the Right Time.

  7. Jason said:

    LW-

    You know, I really wish there were a way to have an honest critique of one’s flirting skills, without it being one of those creepy pick-up artist scuzzbags. Maybe there’s a business opportunity out there.

    We all have the friend or acquaintance who has negative game. (game, here, meaning ability to interact with dating prospects without drawing a restraining order). In my experience, I am at my most attractive to others (i.e. people convey sexual interest in me) when I am absolutely not trying. Not “trying not to try”, but actually not trying. If you go on a date with an agenda, you are dead before you start. There was something about the way you described your recent date with the woman with impressive cleavage that was off-putting. It was vaguely dehumanizing- I know it wasn’t intended that way, but it sounded like you wanted to just date the boobs, not the woman.

    • JenniferP said:

      What would have been cooler if he told us the subject of the conversation that was so great! And what about the woman was so great and unforgettable? (Besides boobs).

      He was being honest about lust, which is fine and not creepy – we’re in the confessional here, a little bit – but the way he describes the conversation makes me not believe that there was ever that real spark. He was always thinking about his next move.

      • Jason said:

        Yeah. It felt like Agenda-based conversation. There was nothing organic about it.

  8. O'Doyle said:

    Delurking to add: if you decide to ask your friends why they put you in the friendzone or a date why she rejected you, you need to be prepared to take it gracefully.

    I’ve had friends ask me why I wasn’t interested in them in the past and 100% of the time they took it horribly. I’ve been called names, been yelled and screamed at, been hung up on, told I’m negative and it’s obviously just me, had my faults thrown in my face or told that I’m shallow/defective/wrong, etc. Then they try to browbeat me into giving them a softer assessment or a lie.

    Those reactions have caused me to not want to answer questions like that at all or I soften and lie when pushed to answer because it evens happens after I first say “Are you going to get pissy when I tell you?” and they promise, promise, promise they won’t react badly. And those reactions caused me to withdraw my friendship from those men because it changed my opinion of them.

    It’s hard to hear the truth sometimes. But if you truly want to know to better yourself, listen to them and accept what they are saying. Don’t get mad and remember, YOU ASKED. If you cannot handle it, don’t ask.

    • JB80 said:

      I’m sorry you had those experiences. I’d actually appreciate a girl being honest with me and telling me why she didn’t find me attractive, so I can change it or at least know what it is. It’s immature idiots like this who can’t handle criticism who ruin it for the rest of us.

  9. You guys are all amazing. LW: flirting sounds like a good place to start for you – most of my guys-I-never-imagined-as-anything-but-friends are abysmal flirters and never put off a vibe of interest in girls – perhaps trying to be non-threatening, but ultimately becoming a non-entity.
    And yes, sometimes it’s just waiting to meet the person who appreciates what you have to offer in the way you have to offer it. In the meantime, trying and failing is better than giving up, because you always learn from it (or you should). And living a full life is better than overthinking it because then you have something interesting to talk about on your dates.
    Also, I can’t recommend being a Super-Advanced-Premium Subscriber enough! It’s worth EVERY PENNY, right y’all? : )

  10. Christina said:

    “If I were to put into words the thoughts they inspired, it would be something like, “she has nice boobs; I hope this date goes well so I can see her naked later.” I can’t exactly say that. Or can I? Maybe I have this all wrong. I was just given to understand that that sort of thing is objectifying and demeaning, particularly during a substantive conversation”

    If you let the conversation guide the compliments you can pull off even very personal remarks about the other person’s appearance without coming off as creepy. Just before we hooked up, while we were still inching our way out of the friendship zone, a conversation on feminism between an ex and me turned to men ogling women’s chests. I mentioned that this had never been a problem for me, perhaps because there’s not much there to ogle at. A little bit later in my ex interrupted the conversation to tell me that men probably do check out my rack and he knows because he just did it and he’s caught himself doing it a few times before and had to check himself so that he doesn’t come across as rude. I don’t know if other women would find that inappropriate, but his tone was one of sharing a neutral piece on information I might be interested in, it fitted in naturally with the conversation, I responded by laughing and then we quickly picked up the discussion we’d been having before. It didn’t feel objectifying or demeaning at all and it did let me know that he was at least physically attracted to me, which I hadn’t been entirely sure of up till then (he also is very good at coming across as super-friendly).

    I’m not saying that you should from now on compliment all your dates on their boobs. But perhaps if you don’t treat your attraction to a woman as inherently objectionable and offensive and a no-go area for conversation, it might make it easier to convey it.

    Also: have you tried online dating? Because at least then your orientation and (general) intentions are right there on your profile for all to see.

  11. The Guy Who Wrote the Letter said:

    So the consensus of the advice seems to be that the approach I take is generally the best one, as far as anyone can tell. I suppose that’s good to know, but it’s still frustrating. It’s hard to keep putting yourself on the line emotionally when the odds of success are so low. It’s hard to be confident, when all the evidence shows that confidence is unwarranted. It’s hard to trust your instincts, when every time your instincts say, “she’s really into me”, it turns out all you were picking up on was her interest in you as a friend. It’s hard to feel sexy when no one wants to have sex with you. If I were to try to take a personal assessment to answer the question, “why would someone want to have sex with me?” I would have no idea how to answer that question because I get so little positive feedback.

    Anyway, I would like to clarify a bit what I meant with the boobs story. The point wasn’t that I was thinking about her boobs the whole time and only paying attention as a means to get to hook up with her. I barely thought about her boobs at all, and when I did, they were fleeting thoughts that I never even considered vocalizing.

    • It’s hard to keep putting yourself on the line emotionally when the odds of success are so low.

      Dude, the odds of “success” (which is what, exactly? sex? love? a long-term thing?) are low for everybody in exactly the same way. Perhaps you are sending out some “I am a special snowflake of misery” vibes.

      • dustyrose said:

        I’m not sure that’s true. Some people just have better luck than others when it comes to dating–or sex, or whatever it is they’re looking for. Some people are pretty much constantly in relationships (which doesn’t necessarily mean they’re happy, but that’s another story), whereas other people get rejected a lot, for reasons that may boil down to nothing but bad luck. I’ve been there, and it sucks. It’s hard to stay confident when you get rejected every time you put yourself out there, and that’s not something everyone goes through.

        • But “some people have better luck” doesn’t mean that you are the Unluckiest Person in the World, you know? I totally get that it’s sucky to be rejected multiple times, and I think the letter writer did a smart thing in seeking some advice about what to do with that personal history. But he’s also rejecting every response because it doesn’t fit with the image of Those Lucky Bastards versus Poor Single Me. Sorry if that comes off as cranky, but when people write to columnists asking “How can I change my situation/behavior” and then don’t accept the answer, maybe they don’t really *want* an answer.

          • The Guy Who Wrote the Letter said:

            There aren’t really very many changes in behavior that anyone has suggested. Most of the suggested behaviors to adopt or avoid are things I already do and avoid.

            The one exception is to try to have more NSA sex, but I’m not interested in NSA sex.

          • JenniferP said:

            EUREKA!

            I have diagnosed you. You are Painfully Literal Guy.

            Nice, not bad looking, friendly, not unloveable, not without hope, just a little bit on the literal side. You have trouble picking up on subtext, pretext, or entendres so you don’t know how to navigate those little awkward, sexy pauses that make flirting possible. You pay very close attention – a good quality in a friend, lover, and employee! – but you are the guy who often says “But you said…” “I thought we were…?” because you’re keeping close track because you’re a little too focused on the details.

            However, there are Painfully Literal Women! See, for example: Lesley Knope. Does Lesley Knope understand hints? NO. Does that make her undateable? KNOPE 2012.

            Continue asking directly and spelling it out. It’s the only way for you. The rest is up to luck and the feelings and attractions of others.

            CASE CLOSED. :Makes satisfying Law & Order gung-GUNG noise:

        • Zweisatz said:

          When I read things like this, I imagine people being really obviously desperate. The point is, to me it’s VERY important if a person is confident or at least … seems to feel good in their body.
          If someone is full of self-pity, I feel this weight on me to make them feel better about themselves and this is not my job. But if they can take care of themselves, have hobbies, have opinions, are respectful towards any group of people I can think of and I like the rest of their character, too – why not give it a try?
          But if people don’t communicate much, don’t have opinions of their own or don’t articulate them, are disrespectful towards others etc. etc., this decreases my opinion of them.
          I don’t want to take care OF someone I want to have a nice date WITH someone.
          The problem is, people with desperate vibes often haven’t cultivated these traits. That’s THE thing, in my opinion.

        • bellacoker said:

          Hi. I’m one of those people with better luck and I want to give you an insider’s view of what that’s like.

          1) It goes in phases, it’s totally feast or famine. One month guys will get out of their trucks at stoplights to ask me to go see a show with them, the next, the guy at the gas station won’t even make eye contact.

          2) During the feast time, everyone’s like, What’s your secret? OMG, you live such a charmed life. (Answer: There is no secret.) During the famines, no one wants to hear about it because one time some guy got out of his truck at a stoplight and asked me to go see a show.

          3) I, like the letter writer, am a highly specialized person, which means I get asked out by a lot of people and go out with a lot of people only to find that I projected something on them which is not really there. Sadly, the heart wants what it wants and mine is still looking. Then I have to say, Hey, I’m sorry, I know you like me but I’m just not feeling this. And then there is a long, awkward car ride where they say things like, But I don’t understand, I thought you were having a good time. That sucks. For both of us.

          4) Sometimes I go months and months without meeting someone who sparks it for me, sometimes nigh on years. But instead of looking back and going, okay, this is within the realm of normal life, excellent, proceed, my little hater goes, Remember that one time when everyone wanted you and your life was a whirlwind of excitement? (There was never really such a time.) I guess you were awesome then and you totally suck now. Maybe you’ll never date again, maybe you’re out to pasture, 31-year old lady. And if not now, eventually, eventually you’ll be old and alone if you can’t remember that magic spell that used to make the gas station guy make eye contact and laugh at your jokes.

          The morale of this story is: Things are rough all around, there are no *charmed* people who have it easier, we all have to live in our own heads.

      • The Guy Who Wrote the Letter said:

        “Success” is reciprocity. She is as interested in me as I am in her.

        I don’t think I give off misery vibes, because in the moment, I usually think it’s working and we’re clicking. It’s usually later, when I ask for a second date, or it’s someone I meet causally, a first date, that it comes up that she’s only into me as a friend.

    • dustyrose said:

      Hi LW,

      I don’t know if I have any great insights for you, but I just wanted to say I’ve been through similar shit, and it sucks. Most likely, it’s not anything you’re doing (or not doing)–there’s so much luck involved.

      I’m 26, and in a relationship for the first time ever. I’ve had involvements here and there, hookups here and there, but mostly just a ridiculous amount of rejection. I know exactly what you mean about getting sick of putting yourself on the line emotionally over and over again, having trouble feeling confident when no one wants to be with you. I know it so well I could have written your letter (and did in fact write a similar letter to a different advice columnist!).

      Meeting my current boyfriend? It was luck, pure luck. My roommate’s boyfriend happened to bring one of his friends to one of my parties, and we clicked. No secret, no magic, just luck.

      I wish I could wave a magic wand and make the same thing happen for you. Since I can’t, I’ll just say I know how much it sucks to be in your situation, and I hope you get lucky soon (literally and figuratively!)

      Also, one post that I found comforting–to the point where I found myself reading it over and over, and even printed it out to carry in my journal–is On Dumb Luck by Kate Harding. A lot of the body image/fat acceptance stuff may not apply to you, but the basic point does. I hope this is helpful!

      ~dustyrose

      • The Guy Who Wrote the Letter said:

        That is a nice essay, and I usually get out of funks like these by telling myself something like that. The question that’s giving me agita though is “Am I doing something wrong that is screwing up the opportunities I do find myself in.”

        • dustyrose said:

          I think at this point, all you can do is either

          a.) accept that it’s just luck, and work on really, truly believing it

          or

          b.) ask some of the girls who friend-zoned you for constructive criticism.

          Or even both.

          Sometimes I wish there were a club for people in this situation, where we could just sit around and commiserate and feel less alone. (I wouldn’t be in the club right now, but I include myself in the “we” because I’ve felt the way you do for most of my life.)

  12. Nobody's Girl said:

    Hey, LW. Just so you know, everyone feels like they have bad luck. I feel like I have bad luck and bad flirting skills, and I’ve been pursued by five people this semester. But I wasn’t into them, and the ones I was into I couldn’t go for (combination of ineptitude and timing), and god I’ve only ever kissed two girls and if it has to involve tongue one really and…

    Generalization: the amount of bad you feel about yourself in a relationship context doesn’t correlate with how badly you’re objectively doing, and so the fact that you feel bad now doesn’t mean you’ll be doing bad forever.

    Also, you are almost certainly not doing things wrong. The things you do are an expression of you and help girls understand whether the two of you are a good fit or not.

  13. Hey LW,

    Can I just give you a big hug? *offers big huge bear hug*

    That was what I wanted to do first. Secondly, have you considered just saying “Fuck it”? I don’t date, but people I know have found themselves happier once they stopped looking for someone and just invested more energy in their friendships, careers, and hobbies. If “The Right One” comes along, awesome, but you probably have lots of awesome things in your life that also deserve attention. And if not, find some!

  14. Former Mayer of the Friend Zone said:

    Ah LW, I know your pain. Quite literally. I spent about 5 years after my first serious relationship having precisely *zero* of the women I was interested in be interested in me. I ended up in the “friend zone” on quite a regular basis, followed by several years of getting into bad relationships where I knew I was settling for women I wasn’t really that into because I thought I couldn’t do any better. I’ve never had a one night stand. I can count the number of relationships I’ve had in my life on two hands and I’m 30. And I managed to meet someone amazing.

    I can solve your problems in four easy(ish) steps:

    1) Stop remaining in contact with women who tell you they just want to be friends. Captain Awkward was 100% right about this. Nothing good will come of this except for you expending your energy on women who rejected you except constantly reminding yourself of what you wished you could of had.

    2) Sign up to a couple of online dating sites, personally in my experience OkCupid was the only site where I actually found women I might be interested in, but your mileage may vary.

    3) Go out on dates with women from these sites where there’s a mutual interest. This will be nice for you because it’s pretty damn clear up front that you’re looking for dates and not friends. In addition if you ask out women you meet IRL, make it clear you’re asking them out on a date. Ask them to dinner or just say would you like to go out on a date sometime. Clarity up front will be really helpful for you. Don’t go on further dates with women where you don’t feel a spark, Don’t stay in contact with women who let you know they aren’t interested (which is what “let’s be friends” means).

    4) Live your life and keep doing 1-3 above. Eventually, many many many first dates that don’t result in second dates later, you’ll eventually start meeting women where the interest is mutual. Trust me, if I could end up meeting someone so amazing I feel like I won the damn lottery, so can you.

    • The Guy Who Wrote the Letter said:

      Actually, this letter was written the night after a date with a woman I met on OKC that I thought I clicked really well with, both online and on the date. The same stuff happens no matter how I meet the woman.

      I’m not a big fan of online dating. My experience has been that I send out dozens and dozens of messages. Of those, only a small fraction reply. Of those, only a small fraction turn into first dates. Of those, none have become second dates. How many quarters would you put into a slot machine that never paid off?

      • Nobody's Girl said:

        Um? That’s how it works for everyone. If you’re feeling disheartened because you feel “unusually unattractive,” feel better: everyone sends dozens of messages, gets only a few replies, and then only a few first dates. Dating is hard for everyone.

      • xenu01 said:

        I am a fat feminist who wears glasses and is very intense sometimes and has strong political views and doesn’t condone racist or misogynist jokes and also likes to MAKE jokes. Cheesy ones. Do you have any idea how many messages I sent out to prospective mates that never got returned? Do you have any idea how many times I went on a date and never got a call back? Do you have any idea how many times I had a guy get way too intense way too fast because he thought I must be desperate for whatever? And what I did was say, “I have this great life and these great friends and dating can be fun, so I will do it sometimes.” It’s like this: if you get turned down approximately 99% of the time, than make that 1% a larger number. Dating is not like a slot machine, ok? There is no such thing as a payoff. Dating is this thing people do where they get to know one another. If it isn’t working for you, try a new way of dating or you know what? Stop dating for a while and get to know yourself better.

        Listen. Stop thinking of women like something you win if you do the right thing. Women are people and people are complicated. Be ok with being single if that is your destiny, and then find out all the fun things about yourself. Stop thinking of yourself as someone special who is having a hard time because dating is hard for everyone. Everyone sends out tons of messages and everyone gets rejected. Stop trying to have 2-hour conversations with strangers be the only way to get close to someone. Sometimes people need to warm up first. Learn how to do small talk and get good at it, ok? Talk about movies and sports and books and politics and the weather. Oh my god, how much mileage could you get out of Occupy Wall Street right now? So much to talk about- what a goldmine! Learn some jokes and tell them. Make fun of yourself a little. Be ok with criticism- you are getting way defensive on this thread/and just plain talking a lot on it, which tells me you need to lighten up a little and maybe learn to sit back and listen sometimes?

        And most of all, stop thinking of dating as something that you do with a goal in mind which is to be with that person forever and ever and think of it as a thing you do where you go out with someone and have fun times that evening and maybe you do it again and maybe you don’t.

        • Jason said:

          This is the best advice ever. Xenu01, you win one (1) internet.

          • I’d like to chip in for additional internets for Xenu01 as well.

          • xenu01 said:

            Haha- thanks for the internet points, Jason and karinacinerina! I will use them to purchase a sledgehammer with which I will smash irritating metaphors.

        • JenniferP said:

          Should I ever create another online dating profile, I’m stealing the first sentence of this comment for my self-description.

          More internet points for you. Though Sweet Machine is giving you a run for your money today and also gets some points.

      • How many quarters would you put into a slot machine that never paid off?

        Aaaaand here is the metaphor that would make many women I know say no to that second date.

        • JenniferP said:

          It’s like he’s been following the #sexkryptonite discussion on Twitter or something.

          “Dating Success,” which the Guy Who Wrote The Letter defined for himself upthread as going out with a woman who was as into him as he was into her, is based 100% and completely on the subjective feelings and decisions of the other person. You can’t control it, and you certainly can’t “win” at it by following a series of steps. We’ve tried to describe it as “accident” or “dumb luck” or “trial and error, mostly error, followed by loneliness and despair, followed by giving up and focusing on other stuff, followed by trying again, followed by maybe more loneliness and despair, followed by a stupid happy accident might work out because at least you gained some self-knowledge and the ability to know it when you see it….maybe” but he’s just not believing us.

        • The Guy Who Wrote the Letter said:

          I’m not the first person in this thread to make reference to the role luck plays in dating, nor am I the first to draw it into a gambling metaphor. I’m not real clear why this crosses the line.

          It seems pretty apt. OkCupid is the slot machine, messages are the quarters. No individual message you send represents a significant emotional investment, but if you stay there long enough, eventually you’ve invested quite a bit. Which is fine, if eventually your investment pays off, and you get an emotional investment back. But if you don’t, then it starts to feel like an emotionally draining waste of time.

          • Painfully Literal Dude explains metaphor! Excellent.

            Look, I know you think that what you said is that OKCupid is the slot machine and messages are the quarters. But in the context of this post, in which you are asking why women don’t seem to fall for you, and the bizarre patriarchy we live in, in which women are constantly treated like playthings for men, there is no way to say “How many quarters would you put into a slot machine that never paid off?” without implying that the quarters are dates and the slot machines are women. I am sure you are going to get very defensive at this, because that has been the pattern with all your comments here, but the metaphor is gross. I am a real live lady who has dated real live ladies and gentlemen–and met my partner of 9 years from an internet date!–so you can maybe just take my comment as constructive criticism, okay?

            Here’s why you’re irritating so many of us who have been participating in this thread, including the Cap’n whose advice you sought: you are either not getting the whole luck concept in the first place, or you are engaging in magical thinking. Imagine you wrote in and asked, “Dear Captain Awkward, I keep playing the slots at the casino, but it never pays out! What should I do?” There are only two answers: 1) Keep putting quarters in, or 2) Stop playing. There’s no other solution! Many people in this thread have suggested ways you can be more direct with women when you ask them out, ways you can express sexual interest without being creepy, ways you can comfort yourself when you’re feeling like The Viceroy of Lonelyland. If you’re already doing all those things–as you keep furtively protesting–then the only answer is to keep playing so you get more chances at these odds, or stop playing. The fact that you keep responding to people who are trying to give you advice that you asked for by arguing with them suggests to me that you really don’t want the advice.

            I mean, really. Here’s how this thread has been going:

            Many commenters: Hey, it’s luck, keep trying to be interesting and respectful and cross your fingers.
            You: But I’m really really unlucky.
            MC: Everyone feels unlucky when they’re not winning, here’s some ways to improve your odds and/or feel better in the meantime.
            You: But how many quarters would you put into a slot machine that never paid off?
            MC: What, ew, slot machines, that is sex kryptonite.
            You: But you said it was all about luck! How can you be grossed out by my dehumanizing metaphor about luck that implies a relationship with a lady is my reward for putting stuff into a slot?

          • JenniferP said:

            @Sweet Machine, thanks for summing this up so well.

            @The Guy Who Wrote The Letter, turn off the internet and go read these two books:

            1. Love In The Time of Cholera, by Gabriel Garcia Marquez
            2. The Heart Is A Lonely Hunter, by Carson McCullers

            Comments on this thread are now closed. I’ll save the Guy Who Wrote the Letter from the pile-ons if he’ll agree to go sit on a cold November evening with a good glass of wine or scotch or beer or a tall glass of chocolate milk, watching the world turn grey and cold and reflect on how loneliness is central to human experience.[Law and Order Noise]

    • The Guy Who Wrote the Letter said:

      That last reply seemed more bitter and cranky than I meant it to. I do appreciate your advice and words of encouragement.

    • The Guy Who Wrote the Letter said:

      On point #1, I’m actually pretty good at getting over people when it’s never going to happen. I can usually will myself to do it almost overnight. I think the key is to avoid “emotional masturbation”. Don’t fantasize about how fun and great and wonderful it would be to be with them. Stop yourself when you catch yourself doing that. Eventually you stop feeling that way and you see them more as a sister.

  15. Guestlove said:

    I suppose I’m the only person who wanted to read that rantlecture. Especially since it it was a complete non-sequitur, I was hoping that the links were to real posts, rather than pictures and a Rosenbaum review.

    • JenniferP said:

      [film professor hat on]
      Ha!

      Watch the movies Breathless, A Woman is a Woman, and Contempt and then also watch Daisies and Vagabond, and let me know what you think that Jean-Luc Godard thinks about women.

      [/film professor hat off]

      • Guestlove said:

        Haven’t seen Vagabond, but I was more puzzled by what the two sets of movies have to do with each other. Or why wouldn’t a pair of movies written and directed by women have a better representation of the inner lives of women than a trio of films more concerned with genre conventions than realistic characters? Come to think of it, it’s pretty rare that a character even qualifies as sympathetic.

        And while I’d agree that Godard’s a sexist, it’s always struck me that he sees women as objects, only reacting to the men around them. Contempt’s Camille, in particular, feels like a personification of how horribly Paul treats her.

        That’s why I was interested in the rantlecture, something to flesh out the ideas and tie it all together. If you’ve got a link or resources to help with that, it’d be much appreciated.

        • JenniferP said:

          I don’t have an actual lecture (or links), the connection is all in my head beyond all the filmmakers being parts of their country’s respective New Wave movements (though Varda gets left out of most discussions of the French New Wave and Vagabond is not actually a New Wave film).

          In my head it goes like this:

          Godard makes films about how women are terrible, unknowable creatures. They are sexy! But full of whims! And childlike! And they fuck you over! Who knows how to please them?

          Varda and Chytilova make films (at least those 2) about women who are ambivalent about the whole love/sex thing. They can be inscrutable (Vagabond, for sure) but their reasons are their own and don’t really have anything to do with men. Why is that lady rejecting me? Maybe because she doesn’t give a fuck and you’re completely projecting motives onto her? Or because she’s young in a totalitarian state and the future looks bleak so why should she play along? The two women in Daisies toy with men to get a little of their own back from a fucked-up world and to pass the time where the only thing expected of them is to be ornamental.

          The problem of the Letter Writer is that he’s trying to figure out why women don’t respond well to him and he can’t figure them out. By glibly referring to those films, in a way that probably only entertained myself, I was trying to say “Maybe because they have their own reasons that have nothing to do with you that can’t be figured out, but not in the way you think.”

          I hope that clears that up for you. Comments to this thread are now really, really, really closed.

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