If you haven’t met in person yet, introduce yourself and tell her how you know her. Look through her profile for information on her family and friends, her interests, and things she likes and dislikes.
If you haven’t tried one of her hobbies, give it a shot. If she loves golf, grab some clubs and hit a few balls. If she loves old movies, ask her for some recommendations. If your crush is an athlete or gamer, try making a bet about whether or not she can do something, like score 3 goals in a row or kill 10 enemies without taking damage.
Many tomboys hate drama, so try to avoid making fun of specific people such as classmates or coworkers. Focus more on entertaining than insulting. [5] X Research source
Eye contact is important, but prolonged staring is intense and off-putting, so glance away every once in awhile.
Self-deprecating humor is a great way to break the ice, but don’t overdo it. Constantly putting yourself down isn’t attractive and she may begin to think you aren’t joking.
Make sure it’s clear that you’re joking around and not actually insulting or criticizing her.
