to flirt or just to shoot my shot?

September 29, 2024 7:16 AM

I’m a mid-twenties woman, I like a mid-twenties guy who is an acquaintance/friendly but not close friends and I’ve been overthinking what to do!

Here’s the situation:
- we know each other mostly through our labor union, of which we are both active members/leaders kind of. we interact pretty regularly in person in a group setting, but haven’t intentionally hung out one on one — though we have talked one on one before several times and it’s always been really nice.
- recently I’ve been trying to put out more explicitly flirty vibes - casual touches, compliments, etc. we were at a mutual friend’s party last week and he intentionally came over to talk to me, and I was definitely trying to give off flirty vibes: sustained eye contact, touched his wrist lightly, told him he looked good. he maintained eye contact and we had a really nice time talking and he stayed somewhat near me for a while at the party but he didn’t explicitly flirt back. but as I said he’s a bit awkward so maybe he didn’t know how to (or he doesn’t see me in that way).
- after the party I texted him and said that I enjoyed hanging out with him and would he like to hang out this week, maybe get coffee or drinks? he took a bit to reply but said yes. ultimately in the process of figuring out what we should do together I chickened out a bit and ended up inviting him to board games with some mutual friends at my place this afternoon — not exactly the intentional one on one hang i was trying to make happen. I think I chickened out bc I was unsure how he felt about me and started questioning myself.

I would love some advice/a gut check on how to proceed. here is my plan at the moment:
- flirt a bit tonight at board games. I told one of my friends how I felt about this guy and she’s coming to board games and will be casually paying attention to see what the vibes are.
- after board games, I’m considering either asking him in person if he wants to go out on a date (which kind of terrifies me) or texting him afterwards (which might seem a bit weird?/not assertive enough?). this time im definitely going to use the word “date” rather than ambiguous “hangout”, though I’m also getting in my head about whether that’s way too serious or formal. im thinking something like “hey I really like spending time with you and I think you’re cool. would you wanna go on a date with me - maybe roam around a bookstore together and get drinks?”

Thoughts on this as a plan? In the past when I’ve asked out male friends, I just texted them and stated how I felt - though I was closer to them and talking directly about our feelings was a big part of those friendships. I think the ambiguity of how close I am to this guy is making this situation feel more complicated - in addition to the contradictory advice on Reddit on this topic really getting in my head.

SO: trust my instincts, or slow my roll?? thanks in advance :)

posted by cruel summer to Human Relations (9 answers total)

Best answer: It sounds like by relying on hints (“flirting“) you’re hoping to get him to make the first move.

Life is way too short. If he’s interested, you’re not going to scare him away by outright asking him out. If he’s not interested that will hurt, but it will also allow you to move on to other prospects.

If he’s worth dating, he’s worth taking the risk.
posted by Tell Me No Lies at 7:24 AM on September 29 [23 favorites]

I'm a woman who has always been comfortable "making the first move" and I can't recommend it highly enough.

People are generally flattered to be asked out if it's done with respect. Finding someone attractive/interesting/whatever is not a thing that needs to be hidden. Asking someone out to coffee doesn't need to be fraught with the perils of friendship-ending rejection drama.

You can make this a low-stakes situation with no possibility of drama if you want to.

Ask your friend to coffee with NO expectations. Try just saying "Hey, I really enjoy hanging out with you. Do you want to go get a drink and look at books together?"

You can text them or call them or whatever makes you feel the most comfortable. You can also ask them that question in a casual tone of voice in person the next time you see them.

If this person reacts poorly to your perfectly flattering and pressure-free attempt to get to know them better then you have your answer and you know not to waste any more time crushing on them.

Good luck, you're fabulous and I hope you have a wonderful bookstore and drinks date with someone special soon.
posted by RobinofFrocksley at 7:30 AM on September 29 [7 favorites]

I'm a man who spent most of my young adulthood missing all the signals like the ones you are sending. I'd just be clear about your interest in dating.
posted by procrastination at 7:39 AM on September 29 [7 favorites]

Best answer: If he is the type to enjoy boardgames with mutual friends he is also most likely the type to be shocked - shocked I say! - to learn that you have been flirting with him and angling for a date. Men receive so many messages these days about how women are NOT “asking for it” that when they ARE it’s completely baffling. Note that I’m not saying we should in any way go back to the horrible ways of the past, and also there are still an overwhelming majority of asshole dudes, but for the most part men who are attractive to women are emotionally intelligent enough to listen to all the hard work of past and current feminists. Unfortunately that means a lot of these men, especially younger guys, are absolutely terrified to make the first move, or even consider that a cute girl might like them back.

Anyway. Try to relax at board games tonight and be comfortable. If flirting happens organically go for it but don’t push it since you will be among mutual friends and it would really put him on the spot. But like, if he touches you, lean into it, hug him hello, etc. Afterwards, or if you find yourself alone in another room together, ask him out on a date directly. “Hey I’d like to go on a date with you. Can we figure out a time we are both free to go to [bookstore] or grab drinks, just the two of us?” You could absolutely text him this afterwards too, but I don’t think you have a reason to be scared of asking in person.
posted by Mizu at 8:17 AM on September 29 [9 favorites]

Best answer: Yes, just ask him out explicitly. When I asked out my now partner (a rather awkward man), my line was something like "Hey, I'd be interested in going on a date with you. But no worries if that's not something you'd be interested in - I'm enjoying our friendship how it is, and I mean that genuinely."

Although:

I think the ambiguity of how close I am to this guy is making this situation feel more complicated

It might be at least worth sorting out for yourself why this is giving you pause, before you make a move. Are you worried that while you're interesting in exploring romance with this guy, you're not 100% certain you're into him? Are you worried that after a few dates, you might end up rejecting him, and that might impact your social circle/union organizing? If you're more curious than sure you're into him, that's fine - there is no rush or uniform timeline before you are forced to decide whether you want to date someone. If you'll feel more confident in your decision if you do a couple of platonic one-on-one hangouts first, that's ok - then do that.
posted by coffeecat at 8:18 AM on September 29 [1 favorite]

Best answer: It's okay to move a bit slowly. You've asked him over, he said yes, he chats you up. I like coffeecat's phrasing. I'd be more specific I'd like to ask you out; we could go for a walk at %place, and I could bring sandwiches. He is pleasant to be with, and maybe something will develop. I've been flirting with someone; it's going to lead to friendship, not something else, but friends are great, and the flirting is fun.
posted by theora55 at 8:48 AM on September 29

Hey, if you don't ask him out you'll always wonder about what could have been.

Respectfully, gently, tell him you'd like to ask him out, and is he okay with that?

Life is short, chances are comparatively few. What do you have to lose?

He may be wondering how to do ask you out. You'll never know unless you try.

I wish you both great happiness!
posted by DrumsIntheDeep at 8:29 PM on September 29

we know each other mostly through our labor union, of which we are both active members/leaders

I'd say: shoot your shot, but only when you're not scheduled to meet professionally for a while afterwards. Just make sure you have some time to process a "no" in case you get one.
posted by Pallas Athena at 7:08 AM on September 30 [1 favorite]

I agree on "shoot the shot" and then have a way to avoid them for awhile. And having to point out "yes, this is a date." Dr. Nerdlove also tends to have good advice as to how to ask someone out and deal if they say no.
posted by jenfullmoon at 8:16 AM on September 30