1. Take her somewhere that you go often. You'll give yourself a lot of credibility and value if you take her to place where everyone knows you. Stop and chat with the staff there. Learn their names and make sure they know yours. It only says good things about you. If you don't have a place like this yet, make one.
2. Take her to an interesting restaurant. It's a lot more fun to go eat sushi or some type of authentic ethnic food than just going to a more common restaurant. You don't want it too be so interesting that there's always something crazy going on and you can't talk to her. Just make sure it is a little different.
3. Relax. The more you relax and show that you're comfortable, the more your date will relax. If you feel like you're getting nervous or tense, just take a deep breath, relax your shoulder muscles and smile. Just focus on having a good time.
4. Get rid of your expectations. So many guys that I meet wrap expectations around everything they do. They think, "buying dinner = she's going to be my girlfriend or wife." If you just spend the time that you're together having a good time, acting like you would around someone you already know well and show that you couldn't care less if anything happens between the two of you, you'll have a much better chance of progressing things than if you act like she's the first girl you've seen in twenty years, acting really nervous and so dumb that she runs away.
5. Don't talk about normal boring topics or "guy topics". If you want to be like every other boring guy out there, talk about what job she has, where she has gone to or goes to college. Only talk about guy topics like sports, lifting weights or something like that if SHE is already very interested in them. Also, don't cling to a topic like it's the only thing you can talk about. If a conversation dies, let it go.
6. Have a story or two that you can tell if you run out of things to say. One of the best ways to keep a conversation going is to have a few stories that you can tell at any time. When the conversation stops, just say, "Anyway," and go into a story. The story doesn't have to be something too amazing, just a little bit different.
Tell a story about a date that you went on where your date did something embarrassing or funny. Women love to talk about relationships and I've found that they are the easiest to come up with. If you're having problems, just grab a girly magazine and read it for 15 minutes. You should find more than enough things to talk about in there.
7. Know a little bit about a lot of things. You can ask me about almost anything and I probably know enough about it to talk for at least 5 minutes. The more you know about, the easier it will be to hold conversations on just about any topic.
8. If your date wants to talk, listen to her. People like to talk and get the feeling that what they have to say is important. This doesn't mean that you should ask her endless questions trying to get her to talk. If she's not talking, feel free to. But, don't interrupt her if she is.
9. Don't try to impress your date. One of the worst things a guy can do is talk about how much money he has, what kind of a car he drives or anything else that comes across as trying hard to impress. If you do have a cool house or car, let her find out when she sees it. And if she isn't impressed by it, don't be surprised. You're much better off by just being a relaxed, fun, cool guy than you are trying to impress her.
10. Have a plan. You should have your date planned in advance. And although you should have it planned, you should also be flexible. If something comes up that could be a lot of fun, don't be so rigid that you can't change plans. Your plan should be more of a guideline so that you always have something to do.
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