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Don't force your smile. It doesn't need to be long at first dating websites and it definitely shouldn't be complicated or make your partner feel uncomfortable. Take it slowly and easy. That may work. Here are some tips. It's great that you're a good listener but you're wrong if you think letting someone do all the talking makes for a great date. Are there money issues? Don't start worrying about what disasters could happen, because that way they are far more likely to. Killing time is one of the best times to engage in conversation with others. If it looks like a duck then it probably quacks so don't think that you are going to reinvent a bad boy from being a bad boy. Nobody likes a gross car! And when we see things that we dislike in others, it often signals that we dislike something in ourselves. You need to be funny, and this is how you do just that! You will know when he comes into your life, no questions asked. I appreciate how [punctual/thoughtful/kind/generous, etc.] you are. It really suits you! Be yourself and don't act fake. Try to keep it short and simple. Although you don't have to have everything in common with someone, it's a good start to find someone who has some things in common. Don't put on an act. Grab her hips and pull her right up close to you so that you have no space in between you. Don't be a player. And, I love your [item of clothing]. It's very effective--but some results may vary depending upon individual personalities. Do some question asking before falling for someone on vacation. A date is supposed to be fun so keep it fun. Send her photos of yourself, from photos to now. This can allow you to emphasize your strengths in whichever area, to signal clearly that you've got the interesting traits, beliefs, or do the activities that your potential mate is looking for. If he finds talking annoying, leave him. When you start to talk make sure you are not arguing. Well some guys find that creepy. Even a lame pick up line can be endearing if you LOOK attractive and SMILE.