(When) Should I ask my best friend out?

Well, here's the deal. This'll be long, but bear with me.

I've known this girl for about a year, and we've been best friends for probably about 4 months. Yeah, I know, some people are thinking "red flag" immediately. We've done a lot together during that time--we've had dinner for just the two of us (both times were trivia nights at local causal restaurants to make things more fun), we've gone to a couple of big music festivals together (one during which she said I would be her pretend boyfriend, mainly to guard her from drunken guys who might hit on her, but still), we're going to another big concert in March and we text each other at least 3-5 days a week. So we've spent time doing things that couples would do together. I've flirted with her rather discreetly and minorly (like putting my arm around her, bringing her close for a short time, etc.) and she didn't shrug me off or react negatively. We don't see each other nearly as much as I would hope, as she works at the local supermarket for about 50 hours a week (six days a week), usually from 3 AM-noon, and I'm working at an 8-5 job. So when I'm free, she needs to sleep lol. Plus I think she's absolutely adorable, and she has said the same thing to me (though in a cute, I guess jokingly/teasingly way, but she wasn't really kidding).

For the majority of the time I've known her (about 9 months) she was in a relationship (a guy I don't know well but seemed like a good guy). She just broke up with him (probably that way, not the other way around) within the last couple of days. She hasn't told me personally, but I noticed on Facebook that she was single--not a stalking move, I just noticed it... don't get any ideas lol. However, I'm still up in the air as to whether or not I should ask her out. I'm going with her in a couple of days to head out to our local bar to sample seasonal local brews (we'd planned this a couple weeks in advance), so maybe I'll get the ball rolling a little bit.

Some of you might be thinking "Hey, if she was hanging out with you for the whole day while she was dating the other guy, what makes you think she won't do anything bad behind your back, like cheat, if she dates you?" She isn't the kind of person that would do that--when she commits to something, she's gonna try her best to make it work. This obviously didn't work out with her now-ex... she broke up with him 6 months ago initially but got back together with him three weeks later, after fighting.

Now, a couple of things. I'm not sure if she likes me back. I'm not very experienced... I'm not sure of many of the signs that people say are indicators that she's taken a liking to you. Most of it is probably because she was in a relationship and didn't want to make things complicated. Also, she probably doesn't know if I know that she's single again. I'm pretty sure it isn't appropriate to ask her what happened, if she's okay, all that jazz unless she wants to talk about it. However, I eventually want to ask her... I really like her, and when I'm ready to commit to a relationship, she's definitely the one I want to date. And I want to do it sooner than later, because I'm afraid of her starting something with someone else because I waited too long without asking or knowing.

I'm uneasy with the consequences that might happen if she doesn't react favorably to my asking her. A couple of months ago, when she was in said relationship, her then-best friend starting making advances on her... playful advances, but advances nevertheless. I'm pretty sure he never asked if she liked him (she didn't) but he spilled his guts to her, rather dramatically, and they're still not talking. I don't want that to happen. I'm not gonna go about doing this even remotely close to how that went, but still...

So I guess the question(s) is/are... Do I ask her out/say how I feel about her? I will respect her decision either way, so I'm hopeful that we'll still be best, or at least great, friends afterwards, even if she says no. And if the answer to that is yes, when should I tell/ask her? Should I wait for a little bit (few weeks) or maybe ask her after she knows I know she's single... possibly at that bar in a couple of days? It just seems rather immediate, but I want to know how to act... I don't wanna screw this up. I'm not trying to put her on a pedestal, but she's probably the most awesome girl I've ever known. And maybe, how to go about doing it without making things overly awkward.

If you're still reading, thanks. And any advice would be greatly appreciated. Cheers!

1 Answer

  • 7 years ago

    That was long lol. I'd say go for it. I made the mistake of waiting once and she started dating a friend of mine. Said she would have gone with me had I asked her before she invested in the other guy. The best way to go about it is not to ask but to try to set up an opportunity to kiss her. Get in her face jokingly and go for it. If she rejects it don't sweat it and apologize for it. You will forever wonder if you don't make a move so just do it.

    If things get weird afterwards just give her about a week and invite her to coffee so you can tell her what happened and play it off as a spur of the moment type deal. You want her as a friend so treat her like one.

Still have questions? Get your answers by asking now.