Should I ask her out, and how?

November 29, 2007 7:23 AM

I really like this girl, but I'm not sure if she likes me. Should I play it cool or forge full speed ahead?

I'm 27, got out of a 5 year relationship earlier this year, finally got over it after a rebound, and am returning to the dating scene. About a month ago a friend suggested I might be interested in this girl who shares a lot of common friends with me.

I started by chatting with her online and flirting on MySpace. For weeks we'd chat non-stop for 5 hours late into the night, though nothing too deep. Sometimes she'd initiate these chats; often I'd initiate them. We have several in-jokes. She went out of her way to mention that she was available.

We've spent countless hours doing stuff in person too but always with large groups of common friends present. I know there are others interested in her too but in person she's friendly with everyone so it's hard to read who she's into. We chat online often but talk on the phone only to arrange events.

A week ago I took the plunge and while chatting online (not the brightest idea) I said it'd be fun to do something not-online and asked if she wanted to go out sometime, just the two of us. I worded the question such that she had an easy, non-awkward "out". In her response, she essentially ignored my question, but responded in such a way that it was clear she had read it. It definitely wasn't a "yes" but it wasn't a "no" either so at the end of the night I told her to think about it. We haven't talked or chatted about it since.

She's leaving for a long trip soon. How do you think I should proceed? Wait it out? Seems like I'd just dig myself deeper into friend zone. Make some kind of bold, in-person gesture with flowers and all? That's usually backfired on me in the past. Accept that I'm reading too much into everything and she's probably not interested?

posted by anonymous to human relations (45 comments total)

Kiss her and you will know.
posted by LarryC at 7:31 AM on November 29, 2007

I don't think she's interested.
posted by grouse at 7:34 AM on November 29, 2007

Too much human nuance is left out of IM and email. Ask for her phone number, call her, and ask her out. If she doesn't give her phone number, it's not going to happen. If you call her a couple of times, and she doesn't return the call, it's not going to happen. If you actually get to ask her out on the phone, you'll have your answer.
posted by poppo at 7:34 AM on November 29, 2007

Being tentative is unattractive. Show her in no uncertain terms that you are attracted to her.
posted by rachelpapers at 7:34 AM on November 29, 2007 [4 favorites]

Always be specific or in my opinion you haven't asked her out on a date, you're probing for her disposition towards a potential future date.

Hey, I've had a great time chatting with you, I'd really like to meet you in person. How about [insert activity here] this [insert date here]?
posted by substrate at 7:35 AM on November 29, 2007

I'd wait until she gets back from the trip and try again. She might be hesitant to start something if shes going to be out of the country for six months. Or she's not interested.
posted by damn dirty ape at 7:38 AM on November 29, 2007

You've shown your hand. For the time being she's decided to hold hers. If I were you I'd let her keep it for the time being.

If you asked her out before the trip, even if she said yes, and even if you went out, and even if she had a good time, you'd spend the whole time she was gone worrying about the momentum dying off and experiences she was having elsewhere changing her mind. And rightly so.

Bide your time. Wait for her to get back, and then confidently ask her out. With all this time to have thought it over, and with the trip acting as a clear divide between two phases of time, I guarantee she'll make it clear whether she wants to go out with you.
posted by hermitosis at 7:39 AM on November 29, 2007

Make a move before she leaves! You'll find out how she feels either way and if she's game, and still feels that way when she returns.. you are set. If not, well maybe you'll have some fun before she takes off. ;)
posted by serial_consign at 7:40 AM on November 29, 2007

Sounds like she was interested before but probably isn't anymore. If you asked her out and told her to think about it and she hasn't brought it up, she's either still thinking about it or just doesn't want to go out.
Full speed ahead romance will most likely scare her off, even if she was considering it before. If she is hesitant, she probably wouldn't respond well to seeing that you are already way way more into it than she is- it adds to the pressure.
I say back off and maybe try again to get coffee once she is back from her trip.
posted by rmless at 7:53 AM on November 29, 2007

a) Probably not interested
b) You already made your move. Anything more will start to make you look needy, and there is no greater turn-off. Your move wasn't the best one possible, but now it's her turn anyway.
c) Don't let this becoming an obsession. Try online dating services, chat with some other girls. Go out. Don't fail to mention that you're doing this in a casual way when chatting with her again. If there is still no reaction from her at all, assume no interest.
posted by Nightwind at 7:54 AM on November 29, 2007

From what you wrote, it seems that you were pretty unambiguous in your invitation. If she wanted to say yes she would have. I can see only two reasons why she did not: either she doesn't want to start something before her trip or she's not interested. In either case pressuring her for an answer is only going to make you look bad.

Let her go on her trip and explore other options while she's gone. When she returns, if she's still acting friendly and you're both still unattached, ask her again. If she says yes, great! If she gives any answer other than yes, you can be pretty sure she's just not into you.
posted by LeeJay at 8:10 AM on November 29, 2007

Well that'll teach me to compose an answer and then take a phone call and hit post without previewing. What Nightwind said. :)
posted by LeeJay at 8:11 AM on November 29, 2007

It really depends on how long the trip is 6 months? That seems too long to wait for a first date. 2 weeks? Okay. If the duration of the trip is an acceptable waiting period, then simply say "I'd like to see you when you return."

When she returns ask her out to something that is clearly a date. That means clearly to her, not clearly to you. In my dating experience, I didn't always hear what the guy thought he was saying. In leaving her an "out", she may have thought you were ambivalent about dating her.

Generally, first dates should be short and very casual. Since you two are already friends and you need to make the leap to boyfriend, I'm going to suggest going for the Holy Grail date night of Saturday. Call early in the week and ask her to do something on Saturday evening. At that point is should be clear what your (and her) intentions are.

In the meantime, go out enjoy all the holiday parties and flirt with all the women.
posted by 26.2 at 8:12 AM on November 29, 2007

Accept that I'm reading too much into everything and she's probably not interested?

Well, I don't know if you should accept it, but you should at least acknowledge that it's a very real possibility. Some people will chat with whoever while they're doing things online. Some people are just flirty all the time. Some people have in-jokes with all their friends.
posted by 23skidoo at 8:17 AM on November 29, 2007

No bold moves with flowers! If she's not entirely sure how she feels, a full-on romantic ambush is going scare her away. I know this seems counter-intuitive, but the best thing you can do is back off and try to set something casual up when she gets back from the trip.

Oh... on preview, basically what rmless said.
posted by the jam at 8:18 AM on November 29, 2007

Go all out now--don't even think about it. If it doesn't work out, you write it off.

If you started out as regular friends from way back, might be different, but here, boldness is better.
posted by Ironmouth at 8:40 AM on November 29, 2007

I agree with the straightforward, succinct, obvious approach. "I'd like to take you out on a date." No more than that.

If she says anything other than yes, she is probably not interested, now or at any point in the future.

And if she really is a good friend, it won't cause (much) awkwardness. It certainly won't be any more awkward than weeks of hints and half-cocked attempts that lead nowhere.
posted by Metroid Baby at 8:46 AM on November 29, 2007 [1 favorite]

Never, ever leave an "out." Accept the possibility for rejection. There's no room for grey areas, this is WAR.

Ok, it's not really "war." Or is it?
posted by waraw at 8:47 AM on November 29, 2007

I'll third armless. You lost your chance by waiting this long to talk to her. The moment is gone. She read it. She ignored it. "She didn't say no" is you trying to convince yourself that you've still got a shot. The more you think this way, the more you'll act like a twit and the more you'll scare her away.

The trip gives you a convient excuse to put some distance between the two of you. When she comes back, say hello, grab a bite to eat and while she's gone, if you see her online, say hello but keep everything light. Next time, don't wait a month to test her out. Ask right away. The worse thing that can happen is that you go down in flames but, come on, that's part of the fun.
posted by Stynxno at 9:19 AM on November 29, 2007

(why did i type armless. god. rmless rmless rmless!)
posted by Stynxno at 9:20 AM on November 29, 2007

I doubt she is interested. But until you ask her directly, you don't know. So man up and take a risk: Call her, or send an email (no I.M. for this -- to easy to sidestep the invite, as you found out), saying directly, "hey, I've been enjoying talking with you. Would you like to get (dinner and a movie? drinks and dancing? some other unambiguous date activity that clearly doesn't involve a big group of people?) with me on (day, time, and place)?"

Any answer other than "Yes!" should be taken as "I'm really not all that into you in that way" -- if she's polite and non-confrontational, she'll probably say something about being busy, but hey, maybe after she is back from her trip, let's catch up sometime, it'd be awesome. And at that point you can continue to enjoy her friendship, but I think your romantic eggs need to start finding other baskets, as it were.

I used to think that "leaving her an out" was the cool and sensitive thing to do, until I figured out that really I was just trying to avoid rejection. But really, rejection isn't all that bad, and it sure is a lot better than investing untold hours into the morass of ambiguity. I'm not saying, grab her and kiss her, or have "I love you!" projected on the scoreboard at the big game as your romantic surprise -- be a polite, well-mannered person, and don't make her feel stifled or pressured. But don't be afraid to ask questions ("do you want to go out with me?") that call for honest answers.
posted by Forktine at 9:29 AM on November 29, 2007

Do people not have phones anymore?

Call her and ask her out to dinner. Like this:

"Hey, it's Jason. [blah blah smalltalk] Say, do you want to have dinner with me this Friday? There's this new Cuban place I've been meaning to try."

If she says some version of "Sure, I'd love to!" you say "Cool, I'll pick you up at 8!"

If she says "Oh, I can't!" you say "How about Saturday?" Then she'll either say "Sure, I'd love to!" or "Can you do Tuesday?" in which case she's just a really busy person. If she says something like "I'm actually just really busy right now", she's saying no.

I don't understand why so many questions about this pop up on AskMe. I'm probably just getting old and don't understand the dating methods of the kids today. But it seems really unreasonable to think that you'll just fall into a relationship with someone without having to, at some point, ask about the possibility of dinner and a movie.

And, erm. It's pretty popular here to give advice about how you can still salvage something, or not, but: in my experience, girls know if they like you or not. It's not very complicated. Either she likes you now, or she doesn't. You playing it cool or being overly needy isn't going to tip the scales one way or another.
posted by thehmsbeagle at 9:35 AM on November 29, 2007 [1 favorite]

Just ask her if she's interested again, this time explicitly. You don't have to have flowers or make a big deal of it, but it has to be clear that you want to date her.

She might not be interested now, but after you wait around for months and then try to build something up again when she gets back from a long trip, she's going to be even less interested.

Or she could be dating someone else. You could end up like this.
posted by ignignokt at 9:36 AM on November 29, 2007

OH MAN DON'T DO IT.

Wait. On second thought ask her out.

What I'm saying is FORGE FULL SPEED AHEAD.
posted by dead_ at 9:42 AM on November 29, 2007

Consider the possibilities.
1) You do nothing. She goes away. You sit around fantasizing, wondering what if ... driving yourself a little crazy, building it up in your mind. When she comes back its built up in your mind enough that you will need an answer. So you make a dramatic gesture. She probably doesn't respond in the way you want as she was somewhere else all along. You feel a harder rejection because its already taken new proportions in your mind.
2) You make another vague invitation. She makes another vague response. You still aren't sure, and leave some door open in your head keeping you from moving forwards or backwards.. maybe you'll shake it off, probably not if you're still chatting with her regularly.
3) You make a specific invitation, ie, lets go to that new ehtiopian restaurant tuesday evening. If she says no, you try to renegotiate another place/time. Until she agrees or disagrees. If you get a yes. It means that shes willing to see you in another capacity (not groups or online). Where it goes from there is anybody's guess. If not then you have a clear answer you can do something with. You'll probably feel bad for a bit, but then you'll at least no that it wasn't meant to be (at least in the current timing).
posted by blueyellow at 9:46 AM on November 29, 2007

i don't think she's interested either. if she was, she'd have jumped on your invitation.
posted by thinkingwoman at 10:39 AM on November 29, 2007

your description of the asking-out is vague. can we see actual wording of your asking and her response?

i've been in too many situations where one party thinks he/she is being clear and the other party did not get the message. IM and email are too easy to misinterpret.
posted by argylekneesocks at 10:49 AM on November 29, 2007

it sounds like you missed your chance ages ago

girls don't have 5 hr chats with guys they wouldn't at least go on a date with...but at some point you fell into the "just friends" category long ago, and then you got your courage up too late!

cut off communication when she leaves, don't initiate it again, when she gets back, if she contacts you, then you'll know you're in, and immediately take her on a date to catch up on things...get a feel for what's happening, and then if you feel there is something going on kiss her right off

but if she does'nt reach out, just forget her
posted by Salvatorparadise at 11:00 AM on November 29, 2007

further, i just don't see the point of asking her now before she goes on a long trip

it's doubtful you'll form some super romantic and monogamous bond in this short period, and she'll probably meet cool guys on her trip and do whatever and thus trod roughshod over whatever you may have built up....just wait wait wait and fire it up on a clean slate when you get back

that separateness, even if you find initial success, will open the door to too much awkwardness w/the distance and doom the thing
posted by Salvatorparadise at 11:03 AM on November 29, 2007

Being straightforward, confident, and unblinking in the face of stone-cold rejection is a rare trait in men these days. If nothing else, she'll appreciate the change of pace from guys who dick around and play mind games or wallow in ambivalence to protect their egos. Be a man! Ask her out! If she says no, big whoop, plan on asking some other girl out the next day. Repeat until someone worthwhile says 'yes.'
posted by np312 at 11:05 AM on November 29, 2007 [4 favorites]

Are you good-looking? And are you in her league, looks-wise?

If both answers are yes, she would have said yes right off the bat.

Sorry to be so honest. But this is the way women think. They are as shallow as we are.
posted by wfc123 at 12:31 PM on November 29, 2007

:)
posted by wfc123 at 12:32 PM on November 29, 2007 [1 favorite]

Are you good-looking? And are you in her league, looks-wise? If both answers are yes, she would have said yes right off the bat.
This isn't exactly advice- what is Anonymous supposed to do, go back and be born better looking in a way that would specifically attract this girl? Anonymous, ignore this silly comment- beauty is in the eye of the beholder, and if this girl doesn't like you, there's always another.

Accept that I'm reading too much into everything and she's probably not interested?
Accept that she might not be interested, but that's not a good reason to not ask her out. Ask her out- after she gets back from her trip.
posted by ThePinkSuperhero at 4:49 PM on November 29, 2007 [1 favorite]

2c: whenever i'm about to head off overseas, there's nothing that could possibly be further from my mind than initiating a relationship. or, in other words, what Salvatorparadise said.
posted by UbuRoivas at 5:08 PM on November 29, 2007

oh, and: About a month ago a friend suggested I might be interested in this girl who shares a lot of common friends with me.

you'd be the best judge of this in your particular situation, but in my experience that sort of suggestion rarely comes out of the blue, but is often more of a (self-appointed?) go-between role, eg said friend has been present when the girl in question has dropped a hint that she finds you cute, or something. of course, that wouldn't apply if she'd never met you at that point. in that case, your friend was just playing the well-intentioned matchmaker.
posted by UbuRoivas at 5:15 PM on November 29, 2007

There are so many equally interesting and attractive women out there why are you wasting your time on one who is both ambiguous about whether she wants to see you and is also leaving for six months?

Get out there, player! Do it now! Stop looking at your computer screen - get out of your house and go to a coffee shop, or better yet a bar. Buying a cutie at the bar a drink is VASTLY superior to trying to mac on one via IM.
posted by wfrgms at 6:40 PM on November 29, 2007

That's way too much talking, my man. Limit your phone conversations to ten minutes and that online bullshit to, like, two. If you want to have a five hour conversation, do it over dinner, then whatever comes after dinner, then whatever comes after that. I cannot stress this enough.

In-person conversations forge a real bond, and the online/phone stuff - for most of us anyway - is fucking boring. You are engaging in a boring activity that only a "friend" is going to do. Chalk this one up in the L column, stop with the interminable internet chats, and just ask them to go somewhere with you. When this girl gets back you won't even notice because you'll be having way too much fun out there.
posted by Optimus Chyme at 7:52 PM on November 29, 2007 [1 favorite]

P.S. Flowers are for girlfriends, not women who you want to date. Never ever ever ever ever make that mistake.
posted by Optimus Chyme at 7:59 PM on November 29, 2007

Get out there, player! Do it now! Stop looking at your computer screen - get out of your house and go to a coffee shop, or better yet a bar. Buying a cutie at the bar a drink is VASTLY superior to trying to mac on one via IM.

That's way too much talking, my man. Limit your phone conversations to ten minutes and that online bullshit to, like, two. If you want to have a five hour conversation, do it over dinner, then whatever comes after dinner, then whatever comes after that. I cannot stress this enough.

The 101st Flying Keyboarders Pickup Artists have spoken!
posted by UbuRoivas at 10:11 PM on November 29, 2007

I was going to give advice based on a personal case, but friends lurk and might recognize, and I'd like to keep that particular bout of awkwardness in the dark where it belongs.

So without the context of personal experience: you waited too long. Cut your losses and go have fun with other girls--offline. Try to do it for the sake of having fun, not for the sake of getting over your attraction to this girl. Heck, try to meet some other girls and ask them out early on just for the sake of doing it. Good habit to get into.

And let's both try to make our moves earlier next time.
posted by postcommunism at 10:15 PM on November 29, 2007

"asked if she wanted to go out sometime" -- This by no means gives her an easy out. If she says no, it sounds like she never wants to spend time with you under any circumstances. If she says yes, it sounds like "any time, any place" which may be more than she wants to say.

As others have suggested, ask her out (in person or on the phone!) for a specific time, place and activity. Then she DOES have an easy out - she can say she's busy then.
posted by richg at 12:02 AM on November 30, 2007

The 101st Flying Keyboarders Pickup Artists have spoken!
posted by UbuRoivas at 10:11 PM on November 29

I'm no pickup artist. I've been shot down more times than Snoopy and the Red Baron combined. But I do okay, and what small success I have comes in some part from recognizing the decreasing marginal utility in godawfully-long conversations that aren't in person. I don't care if you believe me.
posted by Optimus Chyme at 5:42 AM on November 30, 2007 [1 favorite]

Go the opposite way. Make her come to you.

Take the decision from your choosen perspective, not your hopeful perspective.

You had a 5 year romance end this year and have already had another relationship since, and you think you're now 'over it' ?

So what are you 'after' exactly? And more to the point, I'm betting this person is aware of these facts, right? Even if *you* didn't tell her, your shared friends may well have done so...

Hence my initial comment. Hope it works out for you whichever way you go;)
posted by DrtyBlvd at 6:01 AM on November 30, 2007

Ack. Chosen, Choosen, Chosed.
posted by DrtyBlvd at 6:02 AM on November 30, 2007

I hate to say it, but I don't think she's interested. The whole, pretending you didn't hear the question thing is something girls do when they don't want to lose your friendship but don't want to date you either.

Sucks but try not to take it personally. It happens to the best of us.
posted by Jess the Mess at 2:20 PM on November 30, 2007