#214: An object lesson in “overthinking it.”

Dear Captain Awkward,

I’m sure there’s a short and sweet solution to this one, but I can’t seem to see it. Perhaps the Awkward Army can advise?

The very short version: There’s a guy, and he’s cool, and I’d like to maybe get coffee with him sometime and see what happens.

I know, I know, I should use my words! And ask him to get coffee sometime! And do it soon, before I become all invested in a supercrushofdoom! And not hang around becoming friends and nursing a secret crush in the hope that he’ll get a crush on me too!

The reasons I haven’t done this are because of the slightly longer version of the story:

Cool guy is a newish addition to a group of loosely connected awesome people that make up a lot of my social network. Within the broad, loosely connected group, me and two other awesome ladies form a bit of a trio of close and hilarious and got-each-other’s backs friendship.

And the thing is, with the cool guy? My dear friend Awesome Lady Number One kind of got in first. And not in the way you’re thinking, I’m not harbouring a crush on one of my favourite people’s loves. I mean, ALN1 met the cool guy, thought he was cool, used her words to ask him for a drink, and they had a very brief thing that consisted of one date, one drunken sexytime, one decision on ALN1’s part that she wasn’t really feeling it and amicability all round.

So everyone’s a cool grown-up. ALN1 would have no issue with me asking the cool guy out. In fact, she’d be right behind me and find it kind of funny. We know him a bit better now and it’s very he’s more my type and definitely not hers. I guess my issue is that it would be kind of weird for him? Because he is kind of new to this group, and I wouldn’t want him to feel like he was under attack by women one by one when he just wants to hang out with some friendly people…

This feeling of mine is exacerbated by the fact that I haven’t really met anyone that I felt any spark or connection with for a while, so I’ve mainly been having pretty casual sex, which I usually approach by asking some dude if he wants to have sex, or making it obvious to some dude that is clearly after some sex that I would be up for that. So my group of awesome people knows me as being kind of blunt and generally making approaches that are all about the sex, and not about liking someone personally. I mean, this is not always how my love/sex life goes, but it’s where I’ve been recently.

Anyway, I have had some discussion of my crush with Awesome Lady Number 2, who suggests that I should give it some time with the cool guy, continue to hang out with him as friends because we do clearly get on really quite well, and bring up a possible-date some time in the future. This does make sense, and also makes it obvious that this is not my usual type of meaningless sex-only proposition, but an actual “hey, I quite like you and would like to get to know you better in a potential love interest kind of way.”

BUT, I am mildly anxious that if I do that I will end up developing a real crush, being awkward around him, and maybe missing out on the chance of a really cool friend! Because we don’t know each other well enough to actually be friends yet, and I worry that if I’m preoccupied with maybe liking him a bit, and wanting to ask him out but not being able to, I’m going to be too busy harbouring a crush to properly get to know someone awesome. And if I’m nursing a FEELINGSTHING for him, then that has repercussions for everyone else’s friendly relations in the group, because it’s going to be like I always have an ulterior motive in being friendly because I have FEELINGS, and that is AWKWARD TO BE AROUND. (I’m sure this is heading into some sort of GSF, but also I think it is right?)

Obviously I’m overthinking everything, and obviously this is far too long an explanation of a tiny little bit of awkwardness, but take pity and advise me please? This feels like such an amalgamation of things you’ve already addressed that I feel like I should be able to see the answer, but no spark of wisdom has come to me so far.

Awkward wishes,

Awesome Lady Number 3

Hey Awesome Lady, howabout you promote yourself to #1 right now for me, ok? I don’t know those other Awesome Ladies and your love life is not a group effort.

It turns out that I do have a very simple answer for you. If you end up dating this guy (even briefly), you know what’s going to make things weird in your friend group?

Running everything about the relationship, including the question of whether to have a relationship, by the people in your friend group.

Ask him out whenever the hell you feel like it! If you go out and have a nice time, keep the details you share with mutual friends to “We went out. We had a nice time.

This will be good practice for you in terms of a) seizing the day and b) keeping stuff that happens between you and a romantic partner relatively private and not making it everyone’s business.

Good luck!






30 thoughts on “#214: An object lesson in “overthinking it.”

  1. In any event, it doesn’t seem that odd to me that in a group of “loosely connected awesome people”—which sounds like it has quite a few members—one might, when joining it, receive more than one expression of interest over the first few months, possibly even from two people who are part of the same Awesome Ladies subcircle.

    So, given that you’re in the not that unusual situation of (a) finding someone in your circle attractive (b) sharing tastes (to a degree) in attractive people with your friends, you’re cool. However, you are REALLY FREAKING OUT already about how much you like this guy, so, time to exit the FEELINGSBOMBSHELTER.

    ie, +1 to the Captain.

    1. I am thoroughly enjoying the idea of a FEELINGSBOMBSHELTER and am wondering what I shall use to stock it. Also, I believe it needs an appropriately silly hat.

      Most things need silly hats, now that I think of it.

  2. Yeah, pretty much. I got about halfway through the letter when I was like “ask him out already” (then I just kind of skimmed the rest, which is why I am not an advice columnist).

    There are worse problems to have than a series of awesome ladies asking you out.

    1. There are worse problems to have than a series of awesome ladies asking you out.

      This is so true. It will not be a bad thing for Cool Guy to be asked out by all the Awesome Ladies. Unless it’s really obvious that the Awesome Ladies are comparing notes.

        1. I would reply that sharing is great and wonderful among friends, but that a new member of a social group being solicited by all members of a very close-knit group might worry about their boundaries/understanding of privacy.

          I had a very nice relationship with a very nice person that went nowhere – but through her, I met her best friend, and we had a few nice dates that weren’t awkward at all… until this happened.

          Best Friend: *Makes joke, I don’t react* Oh … is that okay? Did I offend you?
          Me: Haha, well, it wasn’t that funny…?
          Best Friend: But have I hurt your feelings? Because of your … past? Oh god I’m so sorry.
          Me: … wait what now.
          Best Friend: Well, you know, I’ve heard all about that Thing in your life that you privately disclosed to my friend and she told me all about it in excruciating detail and we’ve carefully dissected and interpreted everything you do or say?
          Me: … I really wish she hadn’t told you that. If I’d I wanted you to know I would have told you in my own time. I told her because it was relevant to us when we were us.
          Best Friend: Okay, I’ll tell her you said that. I’ll text her right now!
          Me: … don’t text her right now.
          Best Friend: Oh my god have I blown it? Have I ruined everything?
          Me: It’s not that big a deal. But I know you guys are best friends and share everything – I have a BFF too, I know what that’s like – but maybe you could keep my private things private between you?
          Best Friend: Would it make you feel better if I let you read all of our texts about you?
          Me: Strangely, no.

          Of course friends share things, and that’s fantastic. And comparing notes is perfectly fine! I do it with my friends all the time. In this case, it upset me because it was obvious that partner confidentiality was not as important as fuel for conversations between the friends. It made me feel like I was playing the weakest part in some kind of power game. In the case of the LW’s friends, I think the Awesome Ladies are perfectly fine to converse about Awesome Dude – as long as they aren’t dragging each other into their private/sexual/deeply personal lives, which isn’t really fair for anyone involved.

          1. Yuck. I’m sorry that happened to you. I’ve been on the other side of a similar situation — mentioning stuff to people that a mutual friend had told me about but that I had NO IDEA they hadn’t dicussed it with anyone else. Not in the category of major revelations shared in confidence, just mild snark involving mutual friends. At the time I thought if the sharer considered me fair game to receive this snark, it was safe to share it with whomever. Not so! And drama ensued. After which I decided to be way, way more careful about the way I handle potentially weird or iffy information, even if it doesn’t seem like a bombshell to me. Gossip is a sometimes food.

  3. LW, you answered your own question: “I should use my words! And ask him to get coffee sometime!”


  4. LW, as another woman who is prone to the “Hey, do you want to have sex sometime?” pick-up line? The great thing about having a reputation for being straightforward and honest about asking for sexytimes is that it also leads to a reputation for honesty about feelings more subtle than IMMEDIATE PANTSFEELINGS. If you think this guy has heard about this part of your reputation? That’s a good thing, because he knows that if you just wanted casual sex, you would ask him! That you’re going to be asking for “coffee, maybe more time together”? That’s also clear communication! That you’re not just interested in casual sex!

    And if he’s the guy who thinks he shouldn’t date someone who’s had a lot of casual sex, then you know that you don’t want to date him and it’s his loss. Go and continue to be the #1 Awesome Lady in this town.

    1. LW here – this was a really helpful perspective, thank you! Because yeah, obviously the two kinds of proposition are different, and I am basically incapable of not being direct about what I’m asking for. Plus, I’m sure he has listening comprehension! I’m kind of embarrassed now about the extent of my overthinking…

      1. “I’m kind of embarrassed now about the extent of my overthinking…”

        Been there, LW. Just get the hamster off the wheel now, and let it go. ( <—- This is the hardest thing — Good Luck)

      2. Aha, no, it’s totally understandable, especially when the thought is “My reputation is now CASUAL SEX WOMAN which means that everyone will think I am ONLY asking for casual sex, forever!” It’s hard to remember that among people who are not running for the Republican party presidential nomination, that is not actually an assumption that gets made a lot.

  5. Pretend that you don’t know about his brief whatever with other awesome lady. If he mentions having gone out with her, you can acknowledge that you know they went out once, but don’t let on that you know they had sex. Because 1. that’s actually really none of your business and 2. dating around a friend group isn’t scary, but feeling like everyone knows everyone else’s business among that friend group is actually scary… especially when you’re new and you don’t know exactly who runs the coconut telephone and how far it extends.

    If you didn’t know that they had sex, then this is easy. See, he went on one date with a friend but it didn’t go anywhere, so now the field is open for the next classy chick. And if he’s a classy guy, even if he has heard of any of your previous shenanigans, he’ll pretend he hasn’t until you’re comfortable with each other.

  6. Totally fourthing (fifthing? It’s a number at any rate, okay) the “just use your words” bit–I was recently stuck in a similar “should I? shouldn’t I?” situation, albeit for slightly different reasons (dude in question is also my coworker), so I putzed around for the greater half of FOUR FREAKING MONTHS until I finally thought, a little over three weeks ago, THIS IS INCREDIBLY STUPID I COULD JUST ASK HIM AND GET AN ACTUAL ANSWER OF HOW HE FEELS ABOUT DATING INSTEAD OF NEEDLESS OVERTHINKING.

    Literally less than ten words later, that boy I was having pantsfeelings and general warm sappy fuzzybutt feelings for? Sexy nerd boyfriend get!

    And it doesn’t have to be this super long verbose and elegant reason what you want and why; just a simple “let’s date” will totally work. Best of luck to you!

    1. I wish I had come to that realization in college (as well as the realization that, since I’m not at all devout and my parents aren’t at all devout, I don’t have to date Jews, but that’s a story for another time).

  7. Look, girl, you CANNOT know what will happen if you ask him out. There is no way to tell whether he’ll feel like he is getting bombarded by attention from multiple girls, or if you two would be better as just friends, or if your reputation for directness is a problem or an asset, or if you will date for 3 years before breaking up, or if he will confess that he’s secretly the Prince of NeverNeverLand and if you marry him you will have to move to an entire alternate universe and rule a kingdom of cute mice with butterfly wings. Just, there is no way to know.

    But if you don’t ask him out, you know exactly what will happen – NOTHING.

    Interacting with other people is gonna bring some uncertainty into your life, that’s just how things are!


      You really can never know – and to illustrate this, let me tell you what happeend when I decided to use my words and ask out the new cute nerdboy to join my social circle. I obsssed for a while about things to you, LW – the whys and wherefores and what-ifs – and then when I actually *asked* it turned out he was a devout memeber of a small and very strict not-very-well known religion and was not allowed to date. I COULD NOT have prepared for that, there is no way I could have thought it out and gotten ‘prepared’ .

      Life is way more kooky-random that we can ever be ‘prepared’ for, so quit worrying. Ask. Se what happens!

    2. Your final sentence is something I should really get printed on a t-shirt.

  8. Oh honey, I just wanted to make a flowchart for you. Who knows, it may even work.

    [You use your words] ——————————
    I I I
    I I I
    V V V
    [He says no] [He says maybe later] [He says yes]
    I I I
    I I I
    V V V
    [Perfectly fine!] [Casual Date!] ————
    I I I
    I I I
    V V V
    [Achievement Unlocked: Platonic Male Friend] [Bad Date!] [Good Date!]
    <————– I
    [Inform friends when actually Dating-as-a-verb]

    Hopefully that clears things up – there are no terrible outcomes here that are worth Not Dating Him For.

    1. Yup, nope, that didn’t work. Sorry! But the point is: there are comfortable, predictable outcomes to this situation! You will be fine with all of them!!

  9. You are so overthinking this! He’s newish so now is the perfect opportunity to ask him for a coffee. “Hey, did you want to grab a coffee with me some time this week?”

    Also–I went out on a couple of official dates with a friend of a friend about 20 years ago. He’s nice enough, but it just wasn’t there. He still hangs out with that group and we are good friends now. Things aren’t awkward. I promise you, they don’t have to be awkward.

  10. All the important relevant things have been covered, so I just have to say that half-way through your letter I was thinking “Ask Him Out” to the tune of “Normal View.”

    Normal View: http://www.youtube.com/watch?v=N9_L-2k2zxA

    aaaaask him oooout!

  11. I guess my issue is that it would be kind of weird for him? Because he is kind of new to this group, and I wouldn’t want him to feel like he was under attack by women one by one when he just wants to hang out with some friendly people…

    He is an adult, yes? So if being asked out by a past date’s close friend is somehow weird to him, he will say “sorry, that would be weird, let’s just stay friends.” You do not have to decide on his behalf whether he would find dating you too weird.

  12. I have a best friend who is Awesome. And I share lots of things with her! I would trust her with my life!

    But we have known each other now for 26 years, and one thing I have learned about sharing secrets about my love life with her is, uh, I DON’T. Because we live inside a network of complicated friendships and awesome people, and everyone knows everyone else, but everyone doesn’t have to know EVERYTHING about everyone else. That’s my motto. (It’s shorter in Ruritanian.)

    My love life is not a group effort. My best friend is not my therapist. If I fancy someone, she’ll find out when there’s something to find out about. Which is the point after which we stop having coffee together and start having coffee together NAKED.

  13. I’m joining the chorus of ‘ask him out already.’ I was stuck with the crush-harbouring for a while and finally got the nerve to just ask him out. He didn’t feel the same way, but c’est la vie. If you’re thinking of asking him, go for it.

  14. LW here.

    Captain Awkward, thank you for answering my very silly question so soon! I couldn’t believe it when I saw it up on the blog! And also thanks for your wisdom in seeing what I’d somehow managed to ignore – I read back my letter and suddenly thought Wow, this is a letter about people, including (especially?) me, being all up in each other’s business.

    And your advice is great, and if (when!) I muster up the courage to use my words, I will make sure that any hypothetical thing is conducted away from the gaze of curious friends, and without needing to tell people all the gory details. Because yes, that is really not the way to get to know a new cool person.

    [I’m sort of feeling the compulsion, as I’m sure a lot of letter writers probably do, to obsessively clarify a couple of things that I expressed badly.

    a) I think I gave both myself and ALN2 a bit of a raw deal in making me sound like a crazy person who asks permission from their friends to approach a guy, and her sound kind of interfering. Actually, it was more like:
    me: blabber blabber blabber aaargh FEELINGS blabber IS THIS WEIRD
    her: Calm down, you are just being neurotic! But if you’re genuinely worried about it being too soon after ALN1 maybe wait a while?
    Anyway, not really the point, I know.

    b) I guess I made ALN1 and this guy’s liaison sound kind of like public gossip in a pretty intrusive way? This is partly (mainly) because of us being all up in each other’s business, but also partly because of the context of the hookup – ALN1 and I are roommates, there were a few other people crashing at our apartment that night after a concert, and we all went out for brunch the next day during which there was casual mention (from them!) of their hookup. Obviously still nobody’s business but theirs, but maybe this makes the public knowledge thing more comprehensible in this instance? /tedious explanation of minutiae]

    1. Friends talk, it’s ok! It’s just, you were trying to control EVERYONE’s feelings and EVERY POSSIBLE outcome, and that’s impossible! So do what’s good for you.

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