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Captain Awkward’s Dating Guide for Geeks

Ahoy there!

I have a 40-year-old friend who’s very open about his frustrations with internet dating in our geeky friend circle, and recently he went on a date with a 32-year-old woman who, during their date, said that she is looking to have a couple of kids in the future. She didn’t want them straight away, but she’s looking for a relationship that would ideally end up there.

He was appalled by this, and says he feels a) like he was being assessed for fatherhood, and b) that it was unfair that because he doesn’t want to have kids ever, (and I’m sure for other reasons,) she wouldn’t have another date with him – he thinks they’re compatible in other areas, so could have a lot of fun. Most of our friend-group seem to be commiserating with him, but I think he’s out of order. He’s saying that there’s time for her to have a fling with him, but if you’re looking for relationships where (for example) you’re planning to move in together in a year’s time, and start trying for a kid in two, bearing in mind you might not meet someone compatible straight away, you are completely justified in deciding you don’t have time to waste dating guys who definitely will never want children (or any other reason!).

I seem to be in an extreme minority – as a gay woman who’s 40, apparently I don’t understand these things. I suspect that being the type of guy with a long history of fixating on people and not wanting to change anything about himself, it’s convenient for him to decide she would be the next Only Girl In The World rather than look around for more dates. But he’s being given sympathetic suggestions like he should have said he wasn’t sure about kids, and string her along for a bit, or do that AND try to persuade her she doesn’t want kids after all, which is despicable to me, or that this woman was some kind of crazy person who was only after his sperm and he had a lucky escape.

Do you have any suggestions, or resources, to help geeky guys understand that for some (not all) women in their ‘30s, dating can be more serious than for the 40-year-old guys? I’m obviously not getting through – and given he only wants to date women in their early 30s (if a woman’s still single over 40, she’s got too much baggage, or something something? I KNOW! Why AM I friends with him?) this is unlikely to be the only time this will happen.

Why AM I Still Friends With Him

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Hi Captain,

About six months ago, I had to move to the other side of the country for a new job. My now ex-boyfriend and I decided to try out the long distance relationship thing, but then he told me that he would never move to be with me. We kind of floundered for a few weeks after that, then had an ugly, terrible fallout, and I stopped talking to him.

We haven’t spoken since then, despite his attempts to contact me.

Losing him has really messed me up. I was crazy about this guy. I know this is probably going to sound silly, but I really do think he was pretty much perfect. He had this incredible super hero jaw line, a wonderful smile, gorgeous eyes, and had the body of a Greek god. He was smart, funny, and unbelievably sweet. He was the nicest, most helpful person I’ve ever met in my life. We liked all the same movies, TV shows, music, books, food…and the sex was insane. I never had an orgasm until I met him. He was so fucking perfect he didn’t even have morning breath when we would wake up together. I swear, our relationship was like something out of a romance novel. I thought we were going to get married and be together forever.

I’m in therapy and on antidepressants now, because breaking up with him left me in such a mess (like “almost getting fired from my new job” sort of mess). But I’ve been trying to do the usual stuff to help get over a breakup: staying busy, deleting Facebook, hitting the gym, etc., etc. Also, being in a new city where I know no one, I’ve been going to social events to try and make new friends, which has been going well, all things considered. And…I guess I should mention that most of these events have been kinky and BDSM related events because…I am kinky and into BDSM.

I’ve been meeting lots of guys at these social events, and a few of them have asked me out, or asked me to play with them. I usually stand there and quietly compare them to my ex before politely turning them down. Which is very clearly and obviously a sign that I should not be involved with anyone right now beyond platonic friendship.

A few weeks ago, though, I was at another one of these events, and started chatting up with this guy who was super cute. He has this big, contagious grin, and his eyes would light up so bright when he would find out we both liked the same obscure TV show or comic book or whatever. He was one of the first people to make me laugh really hard since I moved here.

We friended each other on Fetlife (a kinky social media website) the day after we met, and he sent me a message asking me out shortly thereafter. I wrote him back, explaining I not interested in dating anyone, but if he wanted to hang out as friends, that would be super cool!

He never responded to that message, but we’ve seen each other at a few more events since then and…I just get the butterflies something terrible when he’s around. He’s just so funny and sweet and so full of passion and life. I mean, he sang to me the other night in front of a bunch of people and it was all I could do to not swoon into his arms. We’ve spent some time talking about our kinks and fetishes and they line up so nice. And what I think is most important is that when we’re hanging out, I don’t sit there and compare him to my ex.

But part of me is worried that we’ll start dating, and then a bunch of old feelings about my ex will resurface. Or I’m worried that this guy will just be a rebound for me, and that doesn’t seem fair to him. Ooorrrr…you know, I start dating him, and nothing bad happens, and it helps me get over my ex more quickly, and everything will just be awesome.

I dunno. What do you think, Captain?

Sincerely,
Whips and Chains Hurt Less Than Heartbreak

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Ghostbusters shooting their plasma guns

“Isn’t it about time we crossed the streams?”

Dear Captain!

My awkward problem is this: I’ve been dating this guy for about two and a half months. He’s nice! I like him! He seems to like me! I’ve stayed over at his place a few times and he’s been to my apartment. But he won’t introduce me to anyone in his life (and isn’t that keen on meeting anyone from mine) and it’s starting to weird me out. Am I overreacting?

We see each other a couple of times a week, usually. He won’t hang on weekends, because he goes to visit his family in another city. Though sometimes, he has said he is going to visit his family and then tells me he changed his mind and stayed home in this town and hung out with his brother all weekend, but he never suggested I meet his brother. It’s like he is Mr. Secret Squirrel about his life. This week he is hosting a friend/ colleague from his company’s office abroad so he told me we can’t see each other as much because he has to work/hang out with this guy until fairly late every day.

At no point did he suggest that I come meet this person and say hi and we have coffee or something low key, though he did discuss with me tourist places he should take this guy. I felt too awkward to ask directly, “hey, your colleague buddy sounds cool, I’d like to meet him”, because he was so cagey (he has not even told me the guy’s name). They are spending the weekend on day trips and I understand why he might not want to invite me to those — he wants to spend time with his buddy & colleague, that’s all cool. But not to introduce me at all seems odd?

I have wanted to introduce him to my friends (I am an ex-pat in this country and my friend pool is fairly small because a lot of people have left (we live in a war zone) but he is a bit dismissive of the things we do – boardgames, Cards Against Humanity etc. Not openly hostile, just “oh that seems weird”.

I have no clue why he doesn’t seem to want me to meet people from his life, and I know it’s pointless to speculate. He is very introverted and maybe it doesn’t occur to him that people can socialize? Is that making excuses for him? Or am I overreacting?

How can I raise this with him without sounding weird or pushy or something? I’m getting really tired of it!

Thanks for any wisdom and insight,
C.

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Let’s play the game where we answer the questions people typed into search engines to find this place. Punctuation added. Wording unchanged. 

1. “My bf won’t choose me over his brothers that are rude to me.

I don’t know what the nature of this choice is, like, probably your boyfriend won’t ever cut off or stop talking to his brothers on your behalf, but your boyfriend should definitely stick up for you when and if people in his family are rude to you. 

2. “When he says he doesn’t have time or focus for a relationship.”

Time and focus may in fact be factors, but also, “he” doesn’t want to be in a relationship with you. I’m sorry, that sucks to hear. Move on from this prospect, is my advice. 

3. “How to turn down a friend down politely convincing her you love but can’t engage in a relationship right now.”

This is the wrong way to go about it. If you don’t want to be in a relationship, just tell her “I don’t want to be in a romantic relationship with you, I’m so sorry, but I value you very much as a friend.” Let her heal for a bit and then you can most likely be friends again. If you use the “not right now” excuse you leave her hanging and hoping, and it’s going to be so much worse.

4. “What it means when a girl say she does not think it will work out.” /”What did she mean by saying we can’t cope with each other?”

Most likely translations: “I don’t want to be in a romantic relationship with you, but I’m using neutral language like ‘it won’t’ work’ to try to spare your feelings.”

5. “How to respond to a compliment on your looks.”

From an acquaintance, not delivered with a leer, like, “You look really nice today?” a good answer is “Thank you.” It’s what people expect to hear and will complete the conversational circuit with maximum efficiency. 

Yelled at you from a moving car? It’s not a compliment at that point. 

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As of August 28, comments are closed. Letter Writer: Go read some books by women, try out some new social activities, GO TO A REAL THERAPIST, and be well.

Dear Captain Awkward,

So I’m a guy, 20 years old and totally devoid of any form of romantic relationship. Ever. I’ve never so much as held hands with a member of the opposite sex, never mind anything else. I’m getting incredibly lonely and yes before you say it, I did behave like a nice guy tm once and just once. I was an ass, I made an incredible fool of myself, I traumatized my friends and worst of all, I hurt that poor girls feelings. She wasn’t the nicest person and took advantage of me, but I hurt her feelings and I made sure when I came to my senses that I apologized, regardless of what she’d done, I messed up. Before all that happened, I was an incredible jerk, an arrogant piece of shit with an intellect to match and zero attachments to anyone. I hated the idea of feelings and I shut them out and didn’t do friends (ironically this is when I received most attention from the females). For most of my teenage years, I didn’t need people and I didn’t need love.

I’m literally petrified of making the same mistake again and of ever hurting another living soul again, I’ve been bad, I’ve made mistakes and I’ve taken advantage of people, now I’m trying, very hard not to be that person again and that includes treating women as people, with thoughts and feelings, hopes and fears and dreams. It’s difficult in the uni dorm I’m in, considering most people I meet socially are either drunk (I’m stone cold sober) or do the whole ‘one night stand’ routine which to me is appalling. The few people I’ve really sparked with are all in relationships.

I’m lonely and very different, I’m eccentric, have eccentric tastes and I’m a lot more mature then most people I meet in most social settings (I’ve been regularly mistaken for 40+ when I was 18) I’m also a romantic whose entire cultural upbringing utterly rejects the idea of genders freely mixing and all that cabal. Pretty much means my social skills are shit. I can out-argue almost anyone and I can debate exceptionally well but I’ve zero social skills that aren’t an argument, sports or one of my passions (which many people do not like) I’m regularly putting my foot in it in casual conversations and I have been told in the past that I am far far too intense. 

On the plus side, most of my closest friends are all female (I do not and have not had romantic feelings for any of them) and they’re great people but they all offer conflicting advice on what my problem is. I’m fast becoming isolated, I’ve zero self confidence and my self esteem has taken a nose dive, a combination of truly looking into the mirror for once and a mystery illness. I don’t think I look handsome, but a lot of people have said that I do. I get really confused and I pick up a lot of body language, but I have no understanding of social cues. It’s like I’m trying to read Swahili.

What on earth is wrong with me? Am I incapable of being loved?

Awkward & Lonely

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Dear Captain Awkward and the Awkward Army,

Long story short: my kind, hilarious, handsome (ex) boyfriend and I just broke up because after two years of things being “great!” we realized that nagging “…but maybe not the ‘forever’ kind of great?” wasn’t ever going to go away. It is very, very sad and very, very hard and everyone is crying a lot and gazing listlessly out windows listening to Bon Iver and wishing this wasn’t our lives.

That being said – we would like to still be friends in a real and meaningful way, and I’m not sure how to navigate this for a few reasons:
- I have some exes who I’m friendly with, but they were all “we dated for 6 months” or less exes, and the kind of “friends” we are is, “we can be in gatherings together and it’s mostly fine and not awkward!” and, “we comment on each other’s funny facebook statuses!” not, “you are the thing that makes me laugh when my day is terrible” or, “you are my partner in crime and adventures” or, “I call you when I just want to talk” friends.

- He has no exes who are his friends, and only one with whom he is on still-in-contact friendly terms.

- We are VERY NEWLY broken up, and I don’t want to mess this up by rushing to friendship before every time I see him and then remember we’re not together it feels like a sharp tug on my Golden Retriever of Love’s leash (you know – that feeling of stabbing knives and despair). But also don’t want to “give it space” until seeing each other turns into this unnatural production.

- I suspect that, in my heart of hearts, I will be unbelievably ungracious about his new girlfriend(s), when their time comes. He is, truly, the Perfect Guy (Funny! Kind! Unbelievably hot! In possession of the world’s best beard! Not into the DC-style of one-upmanship that is the worst!) – and I KNOW that he is going to be snatched up by some really perfect waif-y-type-woman in basically seconds. I “KNOW” this in part because he is amazing and in part because This Is My Greatest Insecurity (jerkbrain says: “What if he dates some blond, no-makeup-wearing, athletic woman next? Will that ‘prove’ that our relationship wasn’t meant to be because I WAS UNWORTHY?’“) and I react to it by having a lot of possessive crazyperson thoughts that I keep mostly to myself, but that eat me up inside.

Can you help me figure out how to navigate, “I love you, but need to be falling out of love with you” and “I want you to be important in my life – but also need to let go of feeling possessive of you?” We’re both going to make an effort to communicate a lot about making sure we’re respecting one another’s boundaries but this re-definition is hard and unfamiliar to me and I just want to cut right to the part where seeing him doesn’t feel like stabbing and I don’t want to push his new girlfriends into volcanoes.

Thanks,
Let’s Be Friends

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Hello Awkwardeers,

I was recently on a double date with a family member, their spouse, and an acquaintance of said spouse. The family member sold it to me as a “try it out and see what happens sort of thing” but I’m not sure if that’s how it came across to the Acquaintance. Acquaintance really seemed to think it was a Real First Date(tm) and now I have no idea how to manage this.

Basically, I’m a single female and I’ve only been completely on my own for a half a year, and I’m only just being able to define who I am and what I want. I’m really not interesting in any romantic relationships, unless the guy is a Super Amazing Fantastic Wonderful and All Around Good Guy. And Acquaintance was perfectly nice, but not enough of a Super Amazing Fantastic Wonderful and All Around Good Guy to get me out of my aggressively chosen singledom. Which is not his fault, I’m just not interested. In addition, I basically had a mini panic attack when he added me on social media after our date/not date. So where do I go from here? How do I let Acquaintance know that I’m not ready for a relationship and probably won’t be for a very long time, and it’s got nothing to do with him?

Thanks,
Awkward Single Lady

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