I need GOLD, Jerry!

December 29, 2009 11:43 AM

When is it appropriate to ask someone out?

I don't know how to date, because when I was younger I never had to. I'm not sure how it worked out any more, but things just seemed to happen until i was 20 or so, and then things got harder, possibly simply because of the decline in popularity of AIM in my age group. After a slump, it's become apparent that since clubs (both the dancing and the common interest variety) don't appeal to me and I tend to be very serious and focused in class-type situations I'm gonna have to learn to date.

So when and who is it appropriate to ask? Long time medium-level friends? Acquaintances? Employees at establishments you frequent? Upon meeting someone at a party? Randomly on the street?

What's the difference between asking on a date and asking for a number? I've never actually witnessed any of these things happening, but I know it must. A lifetime of Seinfeld is not adequate socialization for this!

posted by cmoj to human relations (23 answers total)

And is texting such a thing an option these days?
posted by cmoj at 11:44 AM on December 29, 2009

Whenever You Want

I don't know why this is such a hard concept. Asking for a number is, functionally, asking on a date, you're just agreeing to arrange the specifics at a later time (e.g., hey, could i get your number? I'd like to call you to arrange a date).

It's not hard, it's not rule-governed, it's not fancy, whatever. If you like someone, ask them out, using plain language. Period.
posted by brainmouse at 11:46 AM on December 29, 2009 [2 favorites]

Is texting an option? Sure. Is it a GOOD option? Absolutely not.
posted by brainmouse at 11:46 AM on December 29, 2009 [5 favorites]

Employees at establishments you frequent

Please no... I hate getting asked out at work. To be fair, I've heard of it working out (enough for a date at least), but I've always personally found it very slimy of patrons, no matter how nice/smart/good looking they seemed prior to their attempt at asking me out.

Otherwise, brainmouse is right, you can ask whenever you want. In someone's workplace is just inappropriate, and makes people feel uncomfortable.
posted by sunshinesky at 11:50 AM on December 29, 2009 [5 favorites]

Basically, anyone you're interested in getting to know better is eligible for a date.

Asking for a number means you just got someone's phone number. You may end up going out with this person on a date, or you may become friends. Good for you.

Asking someone out on a date is more difficult than just getting someone's number, but even so, it isn't all that difficult. You say/IM/Facebook message/text, "Hey, I've heard (movie/band/art event/restaurant/museum) is good. It's happening at (specific time) and I'd like to go with you. So, it's a date?"

I think using text messaging to set up dates is totally fine (I'm 22 and female, since that might matter).
posted by SkylitDrawl at 11:51 AM on December 29, 2009

I'm going to be flippant and say "any the hell time you want."

Of course it is not that simple. "Randomly on the street" and "upon meeting someone" rarely work. But if you've established a non-fake rapport with someone - say, after talking for a while at a party rather than when meeting them - go for it.

Don't ask out people on the job though unless you're completely sure they'll say yes (i.e.: you two have been flirting for a not-insignificant amount of time already.) I also wouldn't ask out friends unless you're actually into them or you're both really good at staying cool/casual. It would suck to lose a friend that way.

Personally I stay away from "would you like to go on a date" and swing more toward "want to go get coffee/a drink," depending on when you'd want to plan it for. But that again is staying-cool/casual thing that may not be your thing at all.

(Take all this advice with a 10-lb bag of salt.)
posted by griphus at 11:55 AM on December 29, 2009 [1 favorite]

This probably matters some: I'm 25, male, and looking at being in art school towns for the foreseeable future.

Thank you, so far.
posted by cmoj at 11:56 AM on December 29, 2009

Please think hard before asking somebody out while they are working. I've worked more than my share of service jobs, and I absolutely hated getting asked out at work. I hope it's not your intentions, but it comes across as the customer taking advantage of the polite and friendly manner that the employee is forced to put on.
posted by pintapicasso at 12:03 PM on December 29, 2009 [4 favorites]

Don't ask out people on the job though unless you're completely sure they'll say yes (i.e.: you two have been flirting for a not-insignificant amount of time already.)

This is touchy, because in service jobs, it's often part of the job description to be overly nice/marginally flirty with customers, particularly regulars. It's easy to get mixed signals on this, especially if you're the sort of person who is kind of clueless about this sort of thing. No offense, but the nature of your question suggests you are in fact clueless and says to me that you shouldn't bother trying something so risky.
posted by sunshinesky at 12:03 PM on December 29, 2009 [1 favorite]

It'd be easier to list the times it is not appropriate to try to pick someone up, since there are relatively few of them. So: family reunion; job interview; while there's a restraining order still in effect; at the person's former partner's funeral/deathbed.

In general try to get to know someone a little before asking the person out. You will be in a better position to gauge whether the person is interested in you — and whether you'll want to spend an entire evening with him or her. It'll save you a lot of rejection and bad dates.
posted by orange swan at 12:04 PM on December 29, 2009 [1 favorite]

This is touchy, because in service jobs, it's often part of the job description to be overly nice/marginally flirty with customers, particularly regulars.

You know, I'll honestly take it back if cmoj is straight. I'm a guy and have worked retail and have been asked out while at work and didn't mind it happening - however my experience with that has been "so, you wanna go out?" "I've got a girlfriend." "Oh, okay."

Thanks to MeFi, I've learned that it isn't remotely that simple when women are asked out (regularly being accosted even after saying 'no,' &c) So, yeah, I'll agree; as a general rule, asking women out at work is a bad idea.
posted by griphus at 12:10 PM on December 29, 2009 [4 favorites]

(The above assumes the gay male's experience is closer to mine than it is to a woman's.)
posted by griphus at 12:11 PM on December 29, 2009

It'd be easier to list the times it is not appropriate to try to pick someone up

I will suggest that most women don't want to be picked up at the gym either.
posted by Bunglegirl at 12:19 PM on December 29, 2009 [1 favorite]

Any guy or girl at a gym activaely looking to be picked up is one who doesn't take his/her workouts seriously and therefore isn't dating material.

So says a female friend of mine who is repeatedly hit on at the gym.
posted by dfriedman at 12:29 PM on December 29, 2009

Do you have a big group of friends you hang out with informally? If so, these people are going to be your best allies. Friends-of-friends are always fair game to ask out (provided that they aren't currently attached). They also tend to be good bets, since they probably have something in common with you already. You generally meet friends-of-friends at group events that you go to with your friends. If you're not into nightclubs, that might mean trivia night, movie outings, house parties, potlucks, paintball, or any other kind of informal gathering that isn't too exclusive. Folks who show up to these are great for asking out.

If you don't have a big group of friends, get one! You can jumpstart the process by ...

- becoming a regular at a local bar or coffeeshop. Go at the same time every day, and smile at the people there. Don't make the mistake of asking out the barista or bartender -- they're paid to be friendly and/or flirty, so don't take it too personally.
- taking a fun class. Try dance classes, cooking classes, conversational Spanish classes -- anything where people are there more for the fun of it than for the academics.

One more tip: if you have a friend that's happily paired off and/or of a sexual orientation that's not likely to be attracted to you, you can ask them directly for help. Just ask if they know anyone who's single and might be a good match. There are no guarantees that this will work out, but it can definitely expand your dating pool -- and ideally, your friend will provide you some support and encouragement in your dating process.
posted by ourobouros at 12:50 PM on December 29, 2009

I'm going to go out on a limb and offer an anecdote to further confuse things: back in my senior year of college my (gay) friends always wanted to go to this lame gay bar several nights a week and we always had to sit at the bar (I too was a straight male of your age back then). The bartender was gorgeous and fun and she always doted on us, but I, like the above posters cautioned, didn't want to be that guy and take advantage of the server/served situation, so I never pressed it. We would always chat as she worked and she always returned to my friends and I when she had a chance. I always thought it was because we were the only clientele close to her age (I said it was lame). Finally, one night as we were going out one of my firends asked me why I didn't ask her out, I explained and he said, "You idiot! Why the hell do you think we've been wasting our time in that shit hole!?! We've been trying to you two set up for months! She told us she was game the first time we went in there! How do you ever get laid?" Alas, it was too late, we were both graduating and she was off to grad school in a few weeks and we knew it could never last, but we had some fun for a while.

What a moron I was.
posted by Pollomacho at 12:53 PM on December 29, 2009 [1 favorite]

The easiest answer I can think of is this: Don't Be Sketchy.

If you're interested in someone ask her out. It's as simple as "Hey, would you like to meet for a drink sometime?" Ask face to face. Sure, it feels a little intimidating at first, but eventually you'll come to realize that a "no thanks" isn't the end of the world.

Looking for an easier way than that usually implies being sketchy. Don't be that guy! Don't be the guy who goes to the same shops just to try and land a date with the staff. Don't be the guy who tries to hire someone just to get a date (someone asked that question here just the other day!). Don't be the guy who tries to text "Coffee sometime?" Don't be the guy who preys on people at the gym.

Just walk up to someone you like and ask: "Hi. Would you like to "insert casual activity here". Meeting for a drink is my favorite because it's easy to be chatty at a pub... and if there's no chemistry, you're just there for one drink. If there's great chemistry, you can be there for a while and then move on to something else. Dinner, perhaps? Or a movie?

Best of luck!
posted by 2oh1 at 12:59 PM on December 29, 2009 [3 favorites]

The best thing that you can do is put yourself someplace social where people are meeting each other. Parties, events... there's all sorts of things that you can do.

If you end up having a conversation with someone, and you enjoy it, that's probably your best option for when to ask for a date/phone number.

That said, you'll probably get "no" more than "yes", even in optimal conditions. Don't let that stop you, though. Keep trying, and you'll have some success.

Good luck!
posted by Citrus at 1:45 PM on December 29, 2009

Ah, the early 20s. Everyone goes through this. You stop being surrounded by members of the opposite sex with readily available topics of conversation ("Prof. Schardt is sooo lame!", "I know, right?").

You don't "have to learn how to date", you ARE learning how to date. You're doing it right now. Ask MeFi doesn't have a magic statement that's going to help you. Surround yourself with people of common interests, and get the conversation going.
posted by phrakture at 3:34 PM on December 29, 2009 [1 favorite]

Please, for the love of god, don't ask someone out over a text! (female, 21 years old)
posted by too bad you're not me at 4:05 PM on December 29, 2009 [1 favorite]

Not applying information obtained from tv shows would be an excellent start. Hopefully you'll meet women who would think so too.
posted by xm at 8:07 PM on December 29, 2009 [1 favorite]

A friend of mine advances the idea: "Nobody ever died of awkward." She uses that mantra whenever she's gearing up the courage to ask someone out.

She phrases the lesson far better than I can: QueerFatFemme. Yeah, she's queer, but don't let that stop you from taking the lesson home. Since I adopted that mantra, asking guys out or letting them know I'm interested is much easier.
posted by LOLAttorney2009 at 7:04 AM on December 30, 2009 [4 favorites]

Thank you everyone. This isn't something I'd have marked a best answer for, but phrakture, you're exactly right, and that put it in perspective nicely.

Also, um... the Seinfeld remark was a joke...
posted by cmoj at 4:29 PM on January 2, 2010