Women Love A Sense Of Humor
You could be the spitting image of Brad Pitt, have all the confidence in the world, and have a trust fund that would make Donald Trump envious, but without personality you'll fail with the women that really matter. The women that really matter are the ones that not only have looks, but brains and character as well. These are the types you'd want to marry.
While looks will get your foot in the door, you better have something else to offer or she'll become bored real fast. That's why it's important to develop a sense of humor. Women like to have fun. "Well Duh," I know you're thinking. Unfortunately often times us men have a different view of fun than our dates do. Inviting her over to demonstrate how to install and over clock your brand new Radeon XT-Pro whatever video card is not going to amuse her in the slightest.
That's why I always recommend action dates. Dates where you actively do something together are the best. Treat her like another dude at first. Do you sit around with other guys talking about your emotions while drinking tea and eating crumpets? Hell no! We go out and DO things. Tennis, biking, surfing, video games, pool, rock climbing, you name it. Remember that at the very first you want her to know as little as possible about you (read Listen First if you haven't already). Taking her out on action dates helps keep the chatting away from you and on whatever it is you're doing.
Take her out golfing, to play pool, anything where you can have fun and possibly get close physically while teaching her something at the same time. There's nothing like putting your arm around a hot woman on a date and showing her how to make a proper billiards shot.
Hopefully while you're out on the date you're having a good time with her. Tease her a bit, be slightly cocky but fun, let your sense of humor shine. When I say humor I don't mean that you should repeat ridiculous one liners that you heard from your colleagues at the water cooler. And for God's sake don't make crude jokes with a new date.
Make humorous remarks based upon the circumstances that you're in at that moment. Tease her about her style at whatever activity you're doing. Be playful. If you're not a very humorous person to begin with then rent some Saturday Night Live videos. Buy a book or two on humor. Force yourself to loosen up a bit. Anyone can develop a sense of humor. A genuine, good sense of humor from a normally very serious guy can be extremely attractive to women.
If you can make your date laugh then you're in good shape. It's not just having a sense of humor that's important, it's showing her that you know how to have a good time. You want to show her that you're fun, exciting, and can laugh not only at other people but at yourself as well. It's said that laughter is the key to a woman's heart.