As an introvert, I used to be really, really bad at flirting. But i learned the skill. Let's call it "the way of the introvert" because that sounds cool. Here's what you have to do: Start with the fuglys. Or if you can, the semi-pretties. They need to have one feature you genuinely like. It has to be genuine. Don't be a liar. Never that. You'll come across as creepy. Maybe it's the hair? Most girls work really hard on their hair. Tell them it looks really pretty. And here is the important part: 1. watch her positive reaction. 2. enjoy her positive reaction. You made her feel good. enjoy it. (Ever notice that when an "ok" looking girl smiles she actually becomes quite pretty?) Find more girls to genuinely compliment. all sorts of girls. the girl behind the counter at mcdonalds, the girl you walk by on the street, the girl who sits in front of you in class. don't be a creep about it though. What is creepy? 1. Not being genuine (as i said before) AND 2. expecting to get something out of it. (expect NOTHING in return, not a phone number even). just be nice. just enjoy it. Here's how: You see a fugly but she's wearing a really pretty dress. So, you genuinely say: "you know, that's a really pretty dress! It looks great!" Then as I said before, watch them light up. they'll smile i promise you. they'll appreciate it. Now, enjoy it. enjoy making them feel good. Continue with the fuglys until you feel confident to move to the semi-pretties, and then...etc. (Now we all have different standards as to what makes a fugly and a semi pretty, and a pretty, so don't get hung up on the terminology. Just start with the girls you're most comfortable with.) This is where you want to be. Trying to make the girls feel good about themselves with no expectations. Get comfortable here. Pretty soon you will find that you compliment them, you enjoy their smile, and you'll smile back naturally. Congratulations! You're now flirting. You're now a man and a woman smiling at each other. When you can comfortably enjoy making a girl feel good about herself with no expectation, you're in an awesome place. From here, you will find that there are times it becomes natural to ask a girl out. When you're both smiling, enjoying each other. No expectations. Why not? This is flirting. This is what landed me my wife. I still flirt a bit for fun, but i don't want it to go anywhere. I just still enjoy making a woman feel good about herself. It's wonderful. Go practice. It gets easier and easier. Remember: even baseball players only hit the ball like 40% of the time - if they're good! You'll strike out. Just try to enjoy the game. EDIT: "fuglys" and "semi pretties" is humor used in an attempt to lighten the topic. you know, a joke. Fugly means f-ing ugly. Mostly, the idea is to start with girls who don't intimidate you. Also, if the term "fugly" bothers you, you might also start by removing the object stuck in your rectum.