I'm inlove with my best friend and he's single but he usually goes for the little cheerleader type girl and that's not me he's also kind of a player, but we might be really really good together because we're best friends. What do I do? from Anonymous

1) Ask yourself questions! Redirect the focus from him and the “us” that could be back onto YOU. Stop thinking in “what ifs” and clarify your feelings, so you can do something about them. You are infatuated, not IN love, (because people crazy in love don’t give two fucks about insecurities, they’re too busy trying to be with each other).

Ex: Why do you want this so badly? What you want out of a relationship?  Are you even ready for the skipping of steps that comes with going out with someone you already know well? Are you willing to risk the friendship?

If you can’t answer the basic first two, get to thinking about it because losing your best friend to mutual immaturity is more painful than “unrequited love”.

2) Be good to yourself. You don’t have to be a cheerleader type to have value. Don’t compare yourself to others, do you and fuck the rest. Have some confidence, he already likes you enough to trust you with his friendship.

3) Trust your intuition. If your fears/ insecurities are holding you back from putting yourself out there, either be brave enough to defy them, tell him how you feel and accept the outcome of your boldness; or trust your gut enough to move on to a dude who isn’t a player. At the end of the day we can’t make someone love us, but it’s not healthy to sit around waiting for shit to happen either.

You don’t have to confess your feelings if it turns out you’re not ready for a relationship, but if you choose to, remember this: you have nothing to lose. A true friend loves you for who you are, and/or will have enough faith in the friendship to give you the space to get over it if shit gets awkward. If he doesn’t do this, he’s not meant to be your friend, much less your lover.

You will be fine regardless.

Good Luck!