When is it okay to ask someone out?

June 13, 2010 8:56 AM

Great with online dating, not so much in the real world. How can I better recognize when it's okay to ask someone out?

I know the question is incredibly broad, but this is something that I've been wondering about for a while. While I currently manage to maintain a reasonably active dating life, virtually every time I've met the girl in question online. These never go past 1-2 dates, usually due to a lack of physical chemistry (although a few have been due to other issues, the lack of in-person attraction is the most common).

I've been doing a lot of introspection and believe that the very nature of online dating may be my biggest enemy. Jumping straight into dating a perfect stranger just doesn't seem to do it for me. I believe it might be possible to find someone who is right for me this way, but I honestly don't find the "weeding out" process very fun or exciting - despite attempts to make the dates more fun, there's just too much pressure and too much to measure up against.

Those few successes that I have had dating-wise have been from meeting someone initially in an unrelated environment once or twice (maybe through a group activity or going out with mutual friends), talking with them a bit, we click, and somehow that leads to dating.

The thing is, I've only had that happen to me twice in the past few years: the first time, I asked her out purely for the hell of it figuring she would say no; the second time, the girl was the one who asked me out. Both times we clicked incredibly well and only called it off for reasons beyond our control.

So, my question is how can I increase the frequency of these sort of dates without looking creepy or desperate? By this, I guess I mean when is the appropriate time to ask out a girl I've only recently met, say through a mutual activity? I'm afraid that too soon makes me look like a creep, too late and she might lose interest. As of now, it feels like I have no idea when it's acceptable, short of having a girl flat out tell me "maybe we can get a drink/coffee/etc sometime" or something equally obvious. I can sometimes recognize things like flirting and other indirect cues, but am horrible at interpreting them - for example, I can't tell the difference between "I'm just having fun" flirting and "I'm doing this because I like you" flirting with intention.

Again, I know this is a rather broad question, but any suggestions/advice/etc are welcome...

posted by photo guy to human relations (13 answers total)

It is not okay to ask someone out if she is married, engaged, or a member of your immediate family. Otherwise, it's okay to ask someone out any time you think you might want to get to know her better for the purposes of dating. The worst that can happen is that she'll say no. But if you haven't otherwise been acting creepy (in which case she already thinks you're a creep), she's not going to think you're a creep because you asked for her phone number or offered to take her to a movie some time. Even if she says no, if you ask her in a respectful manner, it'll be okay.
posted by decathecting at 9:01 AM on June 13, 2010 [1 favorite]

If you've had a conversation with enough depth to have any idea what activities she enjoys, you may ask her to enjoy a specific event or activity with you. At a specific time.

'Coffee or drinks sometime' does not feel like a date. 'bird watching this Saturday afternoon/join me for hiking with the local outdoor club/come check out this great sushi bar on friday night' is more likely to feel like a date to me.

Of course, I am one woman, so this is anecdata, but if you invite me to Denny's, a tv marathon at your house, or anything else that I'm not interested in, I'll be disappointed because if I want you to ask me on a date, I will have dropped some hints about good ideas. If talking to me gives you no idea what you might invite me to do, I'm either not interested or you aren't listening.

If it's the latter, you have some shot at guessing an activity that will get me to say yes. But if I'm interested and you suggest something that I don't do (like, 'let's go smoke a blunt!') you will turn me off pretty quickly.

Um. I guess the take away here is, do the best you can with the information you have. Sometimes you'll get a nibble, and sometimes you'll be off the mark. But if you never ask, I (and many other women) won't say yes.
posted by bilabial at 10:02 AM on June 13, 2010

So, my question is how can I increase the frequency of these sort of dates without looking creepy or desperate? By this, I guess I mean when is the appropriate time to ask out a girl I've only recently met, say through a mutual activity?

Immediately. "I really enjoyed meeting you at Bird Watching. If you're not seeing anyone, I wondered if you'd be interested in getting a cup of coffee."

That leaves plenty of out for the person if she is not interested, and is not creepy.
posted by DarlingBri at 10:11 AM on June 13, 2010 [1 favorite]

Right away! Not creepy at all, as long as you're not asking every single girl out that you meet. The times I've had a guy forthrightly ask me out on a date-date (as opposed to a more cautious approach) after just having met him in a social setting I've been really flattered and excited, even if it didn't work out at all. In fact, the mere act of asking in a confident way made them more attractive to me, even if I hadn't considered them at all at first.

Also, it's my impression anyway that as online dating becomes a universal, people are starting to ask people out offline more quickly too -- there's less investment in a first date in every setting. So ask away, grasshopper!
posted by yarly at 11:04 AM on June 13, 2010 [2 favorites]

Are you hesitant because you're worried that you'll come off as a creep or because you're worried she'll reject you? If it's more the latter, the only answer is to ask, ask, ask and you'll get over it.
posted by pollex at 1:05 PM on June 13, 2010

Yes, immediately! If you've made a connection with this girl, go for it. Now, I wouldn't ask a lady out if you didn't have a conversation with her first, but even a "HEY, WE BOTH LOVE... I don't know... fine: BIRD WATCHING!" is enough to ask her out. Do it man.
posted by Lizsterr at 1:41 PM on June 13, 2010

A frustrating thing for many women is when men seem interested in us, but WE can't figure out if they are or not because they say all sorts of generalized things and then never act on them. "If you're not seeing anyone, would you like to go bird watching some time?" isn't generalized, because you do have to get the whole 'are you attached' thing out of the way first.

I often tell young gentlemen that Mr. M. got the girl because he was decisive, unlike every guy who acted interested, but required me to parse meaning of gestures and vague sentences, and never actually took action.

I also like the "get a cup of coffee" suggestion over something that requires more involvement because it's low-risk. If you hit it off, you can say, "I had a great time, woudl you like to meet for dinner/movie/birdwatching next weekend?" and if you didn't, you can say, "Thanks, I enjoyed the evening, see you soon" and move on with things.
posted by micawber at 2:29 PM on June 13, 2010 [3 favorites]

When I was single, I never online dated but I did attend events that were geared toward singles, which fell into two specific categories: (1) things that were geared specifically for singles. For example, I joined a single volunteer group where I met my husband and I went to a dinner that was meant for single young professionals. (2) things that weren't meant specifically for singles but were likely to have a lot of single men attending (I joined an outdoor hiking group). The great thing about the "singles" events is that you know that everyone there is single and looking, so it's sort of expected that you would ask someone out. I also found that when I attended these types of events I would meet people who would then invite me to other events, and so that gave me an opportunity to meet even more people. I think the thing about meeting in person is that you can exclude a lot of people real quickly. For example, I met my husband at a dinner and I knew when I walked in the room that I was interested in him and then within five minutes of talking to him I knew we'd get along. With online dating, I think you have to waste a lot of time dating people you are not interested in. So I would try and see if you can find something in your area like single volunteering, or speed dating, or something like that where you will meet a lot of single women in person.
posted by bananafish at 6:26 PM on June 13, 2010

Thanks for the answers so far everyone! Regarding my original question, I was curious mainly about asking out someone you meet in the context of a group event not specifically geared towards singles. For example, I'm active in a couple of photography-related groups locally and recently joined a hiking/climbing group. Since I've had such good luck with these sort of groups in the past, I'd really like to try meeting someone in this context - but I'm never sure when or how is the best approach in that venue.

The best I can usually come up with is "say, are you free (tomorrow/next weekend/some other specific day)? I'd love to talk more about (common subject), maybe we can get (dinner/coffee/etc)?" or some variant thereof. I know it's not asking out on an actual "date", but it seems to me that I'm obviously showing interest yet leaving an easy out if she's not interested. To me, the approach DarlingBri and a couple of others seem to suggest of asking "are you seeing someone? If not, let's go out" right away to someone I might have just met seems to me like it's coming on a bit strong. Doesn't it seem like it's better to spend some more exclusive one-on-one time with them first, see if you continue to click, then move on towards something more like dating?
posted by photo guy at 7:43 PM on June 13, 2010

The disadvantage to what you're proposing is that it makes it tough for a woman who's not interested (or not single) to respond. I absolutely hate responding to something like that with, "Sure, I'd love to talk more, but just so that you know, I have a boyfriend." It feels really presumptuous, because maybe the guy is just being friendly. So (assuming I'm not interested in dating the person) I'm put in a spot where I either have to say, "Sure, that sounds like fun!" and risk leading the person on, or "No, thanks" (and risk being rude and/or losing out on a friendly activity).*

I recommend something like "I was wondering if you'd like to go on a date sometime" or "I was hoping I could take you out to dinner this Friday" or something that makes it very clear. It's not at all creepy, and if she says no, you can make it 100% not creepy by not pressing the issue, not seeming crushed, and continuing to be friendly.

Good luck!

* (Actually, I suppose I could say: "Yes, and let's also invite Sue!")
posted by cider at 9:04 PM on June 13, 2010 [2 favorites]

@cider - I know you have a point. I don't know why exactly, but using the word "date" with this sort of proposition makes me uncomfortable for some reason. I guess it sounds okay, but in my head it sounds like I'm overdoing it and should dial it back a shade. I guess part of this is just a result of my overall lack of experience with dating and just about everything related - I sometimes wish I could just skip the initial part of this, considering how stressful it seems to be...
posted by photo guy at 5:53 AM on June 14, 2010

Try this: "I'd love/like to see you again" coupled with an invitation for something specific. That way you avoid the clunky term "date" but you leave no question about what you're asking. The key is to convey that you specifically want to see her again, rather than making it sound like you really want to go birdwatching or whatever. If you say "say, are you free (tomorrow/next weekend/some other specific day)? I'd love to talk more about (common subject), maybe we can get (dinner/coffee/etc)?" then it's kind of ambiguous.
posted by yarly at 7:06 AM on June 14, 2010 [2 favorites]

Look, if what you're saying is that you'd like a way to spend a bit of time one on one with someone to see if you like them before asking them on a date, then I think you're splitting hairs on the definition of a date but sure, let's go with that.

"Hey, I enjoyed meeting you at bird watching. Would you like to grab a cup of coffee next week?" is fine.

Assuming that goes well and there is no mention of a boyfriend or girlfriend, you can move on to "Coffee was fun, thanks. Can I interest you in dinner on Friday?" which is clearly date-territory.

Job done.
posted by DarlingBri at 9:09 AM on June 14, 2010