Help me at least TRY to flirt with my friend
December 31, 2012 4:21 AM   Subscribe

Seeing as how I was an utter failure at my LAST crush, I’m determined to do things differently and boy do I want to move on from that nightmare. Help me figure out how to do it.

Mini backstory – 28 year old lesbian just starting to come out (it’s been a little over a year) and navigate dating and flirting with intent. Very slim dating history with guys, and they did all the work anyway. Still have not been with a girl. Making a first move scares the *%@# out of me. Being single for so long is beginning to really wear on me - I'm increasingly lonely and it makes rejection all the worse.

I’ve recently been hanging out with someone that I’ve known for a little more than a year. She is also a lesbian. We hadn’t really hung out one on one much or anything, and she got into a fight with some of my friends and they all had a falling out, which led to me kind of avoiding her a bit. Not being mean to her or anything like that, just not really engaging her. I didn’t know her very well at the time anyway, so it wasn’t like I was ditching her or something. Recently though she has moved into my town and we have more mutual friends.

She reached out to me to hang out a couple times and I accepted and we had fun. Mostly in groups and such. But recently we’ve been in touch/hanging out a bit more, mainly with other friends, and both initiating plans. And wouldn’t you know it, I’m kinda crushing on her. It’s probably because I always had a seed of a crush/attraction to her, and I guess the fact that she was suddenly hitting me up a lot, and then us having a few deep conversations about our mutual friends, made that grow into a regular crush.

So, what are some things I can do to steer this in a more romantic direction before I suddenly get lost in friend-ville and am doomed to suffer there for all eternity? This is pretty much all just starting so I have a fresh slate to work with here. There's good signs and bad signs from her end, and she's kind of hard to read at the moment. I probably am too.

I am suspicious of a friend of hers that she seems to be texting a lot, and that is giving a huge blow to my confidence here. I know she’s not dating her or in a serious relationship, and she might just be friends with her, but the thought that she might be interested in someone else destroys my resolve and is upsetting me more than I thought it would (whoops, guess my crush is bigger than I thought). I guess I’ll find out about that soon enough. And if she IS into someone else and hasn’t really thought of me that way, is it possible to spark an attraction in her?

I guess some people are going to say "ask her on a date." And that's a possibility, but I guess I'd like to see if I can make this a bit...smoother. I feel like the timing is not right to just ask her out just yet and it would be a little awkward, especially since we started out on the friends foot. I guess I want to gauge or provoke interest a bit more, if possible.

I've been doing a bit more than with my last crush, and we communicate better so I'm a bit more confident. I’ve been trying to do the eye contact thing. Today I mentioned something that made me think of her while I was with family for Christmas. I am going to try to hang out with her one on one more. Any other brilliant ideas? The problem is that when it’s another girl it’s always kind of hazy because you can think YOU’RE being flirty and the other person thinks you’re just being friendly. The thing is, it’s so hard for me to be direct with flirting. Guess I’m just wondering if anyone has any great ideas on how the progression should be, or even if there’s any other lesbians out there with anecdotes about what they did or do in this type of situation.
posted by christiehawk to Human Relations (12 answers total) 5 users marked this as a favorite
Dating is not a game of cloak and dagger. You can try and read subtle cues in her eye contct, her textung habbits, whether she uses egg whites or whole, all that stuff. But that wont get you the answer you want. Ask her out. Friends become lovers and lovers become friends all the time so there is no disadvantage to asking her out without extensive prep work. One thing that will work against you is waiting for the timing to be perfect or believing you have sent enough subtle cues. A simple "hey, I am in to you and would like to go out sometime. I think you are interested too but if not that is cool because I like our friendship too." is sufficient.
posted by munchingzombie at 5:34 AM on December 31, 2012 [4 favorites]

I'm assuming she is out longer than you and has more experience with women? If so, talk to her about that. Ask for advice, how she handled the situation, how she got involved with her first girlfriend - general dating advice for the inexperienced lesbian. It gets the subject on the table and she will likely let you in on what she considers flirt signals. Hence it's easier for you to see if she is flirting with you or what signals she would read right coming from you. It's more subtle than "asking her out". That step comes after successfully being introduced to her flirt signals and recieving or sending them.
posted by MinusCelsius at 5:59 AM on December 31, 2012 [1 favorite]

I think MinusCelsius has a good idea about asking a friend for help with signals, but I suggest not asking a friend you are crushing on for that help. That strikes me as a bit disingenuous and vaguely creepy in a way that might be cute when accompanied with an alterna-pop soundtrack in a made-for-TV movie but is kind of the wrong foot to start off on in real life.

munchingzombie's notion of just saying what you are thinking is better.
posted by seanmpuckett at 6:30 AM on December 31, 2012 [3 favorites]

I know this isn't what you want to hear, but you'd be doing yourself a huge favor if you just asked her out and spared yourself the weeks or months of anxious maneuverings and guessing games. I'm saying this as a lesbian whose fiance did this three years ago, after a semester the both of us spent doing the "hey I like you but I don't know if I should say something" dance*. After a great day out together, she called me up and said this might be awkward but that she liked me - and I could not have been more enthusiastically happy about that (I woke up the next morning wondering if it had just been a wishful dream on my part!). She's since told me that she'd written out a little script to help with her nerves; maybe that could help you, too?

*I realize that since I was the askee rather than the asker, my anecdote might suggest that if you keep on waiting maybe your crush will ask you out too, but I really hope you dismiss that idea. It would have been so easy for us both to have kept on crushing on each other but waiting for the other one to make the first move, and we would have missed out on an amazing relationship. Someone else might have asked one of us out; one of us might have moved away, or even just gotten busy in some other area of our lives - your window of opportunity won't stay open forever! Ask her out, and good luck!
posted by DingoMutt at 6:31 AM on December 31, 2012 [2 favorites]

I guess some people are going to say "ask her on a date." And that's a possibility, but I guess I'd like to see if I can make this a bit...smoother. I feel like the timing is not right to just ask her out just yet and it would be a little awkward, especially since we started out on the friends foot. I guess I want to gauge or provoke interest a bit more, if possible.

Ah, the "newly coming out/I don't want to make a move/I have to feel it out" thing. It's been a long time since I was a freshly-minted gay dude, but seriously, ASK HER OUT ON A DATE.

The lucky thing that we gay folks have is that we have a really small pool of folks to choose from (compared with the hetero population), so people who have dated people in our "Friends" circle are likely to stick around. Heck, I have friends who I've slept with and it didn't work out and no big deal, because there really are only so many gay people in North Suburban Boston.

It's terrifying the first few times, but it's okay to ask someone out. Especially if you're friends with them, and you can be okay with, "Sure, but if it doesn't work out, let's still be friends," or "No thanks, but I like you anyway."

posted by xingcat at 6:41 AM on December 31, 2012 [3 favorites]

I am like you - it's very easy for me to spend all my time having crushes, looking for "signals", etc. And mysteriously, I have dated a lot less than other, more direct friends in my social circle.

It's fatally easy to get into the habit of not asking - are you very "guess culture"? Do you behave the same way in other areas of your life? (I am; I do!) You're at a great time to make a break with that habit!

I have a friend who is, hm, socially awkward. Less so now than a few years ago, but not the suavest apple in the barrel. And yet, that friend - of average looks, not a millionaire software developer, etc - has dated a ton. And it's because my friend trained themselves to ask. Friend got rejected a bunch, but eventually hit critical mass on social skills/asking ability and had a string of successful relationships culminating in a good, solid long-term one.

Also, bear in mind that if you fear rejection but tumble into a relationship anyway, you'll still have to deal with all the rejection/break-up/off-the-rails stress of the actual relationship. Having a positive approach to asking people out (and the accompanying strong sense of self) will carry you through ensuing relationships better than being all flinchy.

Also, xingcat's comment - everyone I know has dated/hooked-up-with everyone else I know, queer-people-wise and straight-nerd-wise (small pools!). I know people who have been through really apocalyptic bad relationship stuff and made up and became friends again afterward - never mind a little bit of "well, she's a lovely girl but I didn't want to go out with her".
posted by Frowner at 6:54 AM on December 31, 2012 [5 favorites]

Also, people can be interested in more than one person at a time. And also, the Person Who Asks You Out tends to trump the Remote Crush Who Isn't Interested Even If You're Texting Them A Lot - the mere act of asking someone out tends to confer a lot of attractiveness points.
posted by Frowner at 6:57 AM on December 31, 2012 [5 favorites]

I am a straight guy, but I have been on a first date with almost 500 women so I will answer.

Do yourself a favor and drop the idea of hoping to be "smooth" about it. Occasionally I was able to line things up where I made my big move in an amazingly cool way. But if I had waited for that, I'd have about 450 less opportunities (including my wife). That ratio is with the added benefit of previous experience and being an above average conversationalist. Since you have less experience, the odds of you doing things in a Hollywood screenplay kind of way are about 1%. Reduce it even further if you are shy, a poor small talker, or generally lack confidence.

You have to ask her out and specifically say the word "date" (since you have a friend-like history). I know the younger generation likes to hedge things by using phrases like "hang out" or "go do something", but the younger generation also has phrases like "limerence" and "friend zone" so draw your own conclusions.

Hmm, I think there was one more thing. Oh yes! Now I remember. Don't worry about how many friends she has, who she texts, or whether you perceive she has a lot of opportunities to date. Would you even be attracted to her if she was a plain-looking recluse with no social life? Any desirable person is going to be a little intimidating so the advice is still the same -- ask her out on a date! (Now, if you ask out ten women and get repeatedly turned down, then...and only you need to adjust your expectations.)

Good luck, you can do this! Even a brutal "no" is ten times better than this analysis paralysis stuff.
posted by 99percentfake at 8:13 AM on December 31, 2012 [2 favorites]

Ask her out. If she says no, what have you lost? It won't ruin the friendship---one of the cornerstones of lady-loving lady culture (in my experience in the US at least) is that everyone stays friends with their exes, and the people they wanted to date but didn't, and the people who wanted to date them but didn't.

It's not like there's going to be a magical "right time" when you'll be hanging out as friends and then suddenly she'll look deep into your eyes and draw you close for a passionate kiss. That's an Ann Bannon book, not real life.
posted by Sidhedevil at 8:54 AM on December 31, 2012

I am dating a woman who initiated things by saying, "I really like you and would like to get to know you better in an intentional way with the possibility of getting physical at some point." I have a lot of experience and had never had anyone be that simply plain spoken before. I almost fell in love on the spot. Her habit of honesty has continued to delight me. I am learning a lot from her. I can't say enough good about a person I don't have to guess with, and know that I can bring things up and be honest about where I'm at, too.

Which is to say: ask her out! Let her know what's on your mind. Believe me, a nice clear No, thank you is worlds better than any number of days and night on the rollercoaster. And that's only if you don't get a Hey, me, too.

Good luck.
posted by not that girl at 9:35 AM on December 31, 2012 [5 favorites]

Based on what you've said in this question, she's not at all into you and you should abandon this plan completely. You are in the friend zone and no amount of flirting will get you out of it.

Did your blood just run cold and did you experience tunnel vision as you contemplated that possibility? Yes? That is the fear of rejection that is keeping you from pursuing her directly, and which is inspiring you to pursue fruitless intrigues in the hopes of maybe someday cultivating something without ever having to take a risk.

It isn't about eye contact. It isn't about how much you text. It isn't about whether you invite her out X times in a two week period. It isn't about whether you laugh loudest at her jokes. The only way to move forward is to address this directly. Ask. Her. Out.
posted by jph at 9:46 AM on December 31, 2012 [2 favorites]

Another voice in the chorus here. You don't get over this hump by guesswork. You have to ask.

It gets easier the more you practice.
posted by ead at 4:58 PM on January 1, 2013

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