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.
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.