Advice on asking a girl out on a date.
It has been a looooong time since I asked a girl out on a date (if you don't count the times I've asked my wife out in recent years). But I learned a lot about it back in the day, and I don't think human nature has changed that much.
I asked people out in high school, but not much, and I was always shy. My first semester in college, I continued in shyness. I don't think I went out a single time that fall. But over Christmas break, the thought occurred to me: "These people don't know me. They don't have any preconceived notion about me. They don't know what my dad does for a living. They don't know about that unfortunate incident in ninth grade. I'm starting with a clean slate!" I also realized that, at worse, if I made a fool of myself I would only see these people for maybe three or four more years.
My first week back for Spring semester, I had 10 dates. Yes, you can do the math. There were days I took a girl out, took her home, and picked up somebody else later in the evening. It wasn't because I had suddenly become so desirable. It was because I had learned some of the following.
1. Be willing to hear "no."
You have the greatest chance of hearing "yes" if you ask. You're more willing to ask if you're willing to hear "no." I heard "no" that first week back in Spring semester than I heard "yes," but I also heard "yes" a whole lot more than I had heard it in the fall.
Don't hint around. Don't wait for it to be her idea. Ask.
3. Stop worrying about impressing her. Just be you.
She will form her own opinion of you regardless. When you try to impress her, you come across as trying to impress her. It's not just that authenticity is more attractive (although it is). You just her to be interested in you as opposed to "someone else" (the fake person you think might be more attractive). You want to make sure that if she wants to go out with you, it is really you she wants to go out with.
4. Suggest a low-level activity first.
Just say something like, "You seem like an interesting person. I think we might enjoy some time together. Would you like to go get coffee/lunch, etc.?"
5. Build on natural points of connection.
Assuming you're not walking up to a random person, you probably are taking part in some activity together already. Suggest, "I'd like to know your thoughts/experience with bowling/tennis/taxidermy/whatever you're both doing." Even if it's in a bar, you have that bar in common. In that case, depending on which is the case, I might say something like, "I'm one of the regulars here, and I don't think I've seen you here before. I know it sounds cliché, but I'm truly wondering if this place is new to you, and if so, what brought you in?" Or, "I'm new to this place. I know it sounds cliché, but you seem familiar with it. I'm truly wondering if you are a regular, and if so, what's the best item on the menu?"
All kinds of variables here—is she by herself or with other people. Does her body language indicate she wants to be left alone? Is she conversing with the bar tender? Are you sitting close enough that you could legitimately become part of an existing conversation?
For instance, yesterday I was at a UPS store. The counter clerk was helping another customer with some shipping problem, and she said, "They said that there was a problem with the label, and they would send you a PNG file, whatever that is." I was right behind him, so I said, "A PNG file is a graphics format. Basically, they said they would send him a picture." She said, "Oh! That makes sense, thanks!" It would have been easy to continue the conversation from there if I had wanted. Neither of them seemed to think it was an intrusion.
6. Be a listener.
Don't interrogate her, but ask open-ended questions and listen. Reveal enough about yourself that you register as being open, but it's far more important to listen than to talk.
7. Be interested in her.
This goes along with being a listener. Before you ask her out, you should have had a conversation of some sort with her. Chat a bit. Don't hide yourself, but keep your focus on her. Dale Carnegie said something like if you learn to ask good questions and mostly keep your mouth shut, other people will think you're a brilliant conversationalist.
8. Leave the door open.
If she says no, be gracious. While "no" means no, also doesn't necessarily mean no forever. It may mean "not right now."
9. Don't try to control it.
Don't steer. Be open. Go where the conversation goes. Then when you ask it will just be a natural part of the conversation—to the point that it would seem weird if you didn't suggest getting together/going out/talking again.
10. Try not to put all your hopes on one girl.
I don't mean that you should sneak around. But if you're feeling like this is your last chance, no one else in the world could possibly live up to this person, etc., you will come across as desperate, and desperate is scary. Even if this person is one in 10,000, there are roughly 60 million women in the USA between the ages of 20 and 50. That means there are 6,000 more "one in 10,000" out there. If you just met her, you can't possibly determine if she's a one in 10,000 anyway. If she says no, you learned valuable information. Move on.
Another part of this: be willing to walk away. A date is an experiment. You are checking each other out. If you had to commit to marriage before you asked for the first date, how miserable would everyone be? It's perfectly OK for you to say later, "You know, this just isn't working for me," and when she exercises that same right, it's not a commentary on you. It just means you're not a good mix. (Yes, I know how hard that is on a gut level. Learning to deal with rejection is one of the biggest lessons I had to learn in order to have the greatest chance of not being rejected.)
11. BONUS: Take it slow.
Allow the relationship to unfold. This is the corollary to "don't try to steer it." Relationships are more like sailing than driving. You may be aiming for a particular direction and destination, but conditions constantly change, so you have to constantly pay attention and adapt.
How did I learn this? Let's just say it took two previous marriages. I'm on my third and last one. Take it slow.
12. BONUS: Don't focus on finding the right person. Be the right person (yourself).
You're not just attracted to. You also attract. Just live your life, while not being a hermit.
13. BONUS: Quit worrying about whether it's a date or not.
For your specific situation, @jay_yow07, you're already having conversations at a bar. In a way, you're already on a date. Just say, "I'd really like to continue this conversation. When can I meet you here again?" You don't have to use the word "date." You're just confirming a time.