One of my friends went through a rough break-up last year (they were in different places in their lives, she didn’t pay attention to him, etc) and he’s been pessimistic about dating since. It’s been about a year and a half I’ve been trying to set him up occasionally, encourage him to get out there and all since he says he wants a relationship. But he’s dead-set against online dating, and he says he doesn’t know how to ask a girl out. I have zero casual dating experience (all my SOs were friends first.) So here are some questions he asked me that I don’t think there is a ‘right’ answer to but he seems to think there’s some average answer:
1) How long does a guy typically wait before asking out a girl (assuming they just met)?
2) How long does it take for a girl to decide that a guy she meets is ‘friend-zoned’?
3) Any other personal advice about dating you could give.
LemonVibe 
[1) The sooner the better. You meet on the street, guy’s heart starts palpitating… he should just ask her then and there if she wants to “get coffee” sometime… or some other such low pressure date scenario that would be carried out in public.
2) Usually immediately. In most cases, a girl will know right away… but never count yourself out because often the best relationships form from solid friendships where the guy was initially friend zoned.
3) Live, laugh, love.
(I got #3 from those cheesy artsy signs at Hobby Lobby. But it works)
[I may not be the best person to ask about typical dating behavior, but as a female, here’s what I’d think/want:
1.) As soon as he wants to. I mean, if someone asks me out, that’s an indicator of interest. It’s pretty straightforward…
2.) Well, my typical interest has gone, see/meet guy, think guy is attractive/fun/awesome/etc, want to get to know guy better, end up friends with guy, now I’m afraid to rock the boat. Basically, you could get friend-zoned…but that doesn’t necessarily preclude romantic interest, it just might make her wary of risking the friendship. And the worst case, you have a new friend, who, by the way, might just know other friends with whom you might find a mutual attraction and interest.
3.) Relax? I mean, I’ve really got nothing here…I’m not an expert on this one. 🙂
[1) The old Singer’s rule of waiting 3 days before you call a girl is out. In this day and age of cell phones, texting, facebook, email, twitter et al, a guy has no reason to make a girl wait. If I like a guy and he calls me soon after recieving my number, I am turned on. A guy that makes me wait, amkes me wonder and give up all together on his ever calling? Guess what, not only have I moved on but it doesn’t set a very good precedent about what kind of boyfriend you will be.
2) There’s lots of reasons we put you in the friend zone. If you are a coworker, or dated a friend, for example, you immediately go in that category. For me, if I liked a guy but he took too long to make a move, I assumed he didn’t want anything romantic and so turned off my romantic feelings for him. Don’t wait so long that she’s moved on! And yes, not to give a guy who is in the friend box because the girl simply doesn’t find him attractive, but I married the man who was once signed, sealed, and delivered in the friend zone.
3) Don’t sweat dating. When you know, you know. Be okay with being single and happy, and stay open for someone great to come into your life, no matter how you end up meeting them!
[1. I’d the others I would be tempted to say straight away, but I’d say sometimes it makes more sense to swap contact info before arranging anything. That way the pressure is off of the other person and you can work out what you’re going to say/ask. Not to mention you can actually get to know them a little.
2. As the proud owner of male genitals I don’t feel I can comment on this one.
3. Finding a partner is like finding a mattress. Some people want one that’s comforting, others want one that’s firm and supportive and some people just want one that other people won’t piss on.
[1) Ask her out right away. Or soon thereafter. It’s super flattering when you meet a guy and there’s an attraction/flirtation and then he asks you out. It’s sooo nice not to wonder “what if”!
2) I agree with what Jasmine said re: the friend zone. In my opinion, it’s never an irreversible categorization – and, honestly, I think most of the time when a guy says he’s been friend zoned, it’s because the girl just wasn’t that into him. Do with that what you will.
3) Be yourself! Don’t try to be what you think girls want. Be happy with who you are and other people will be attracted to that.
[1. A guy shouldn’t wait too long to ask her out. Depending on the circumstances under which you met, you could ask her out right away. If you know you will see her on a regular basis anyway, then asking her out immediately might be a little too forward. However, don’t wait too long.
2. Most girls know right off the bat he is the type of guy she would date (usually based on physical appearance) or not. But one way to certainly put yourself in the “Friend Zone” is to wait too long to ask her out. If you’re too passive in the beginning, she may see you as nervous, unconfident, or even unmanly . . . definitely not boyfriend material.
3. Just as Breck said, be yourself. By being yourself, you will attract the type of girl you want to be with. That’s what really matters in the end. Other than that, just be receptive to women. Don’t rule out people too fast, but don’t waste your time.