As someone who once considered themselves a lame as a middle school/early high school kid, flipped that to an extended fukkery phase, and then settled down: Accept that you're going to take the occasional L. Be that from getting rejected, wasting time on someone you find out isn't worth it later, or what the fukk ever. The number one thing holding people back from anything, let alone relationship s, is being afraid to fail to the point that they don't even really try. fukk that. Try, and if you fail, learn from that failure, and be better. You need to lose every now and then to learn or remind yourself that you don't like that shyt, and stay hungry for victory. And in relationships, fukking up helps you learn what does and doesn't work for you personally, and what you do or don't like. Also gives you the occasional funny story to share in the future. Like others have said, be up front about your attraction to someone, but don't be extra heavy handed with it. Playful flirting gets you in some draws. Overly aggressive flirting will often get your number bushed. The rest is just staying true to yourself. For example, if you know you're corny, just be corny. Women are far more appreciative of someone who's comfortable with being who they are than someone who is clearly striving to be someone they aren't.