For years I've had this problem: I'd say since back when I was 9. Humor became this mechanism through which I preserved my emotions. I once had a rough day in school where everyone teased me and made fun of me, and my mom said 'son it's okay to make fun of yourself', aaannnddd I took it way too seriously.

I started making jokes every waking moment. Granted a lot of them were funny, but most of them were try hard and to this day whenever I'm having a conversation it's easy to get someone to loosen up because of the humor, easy to get someone attracted. But whenever they try to become a friend I use worse and worse jokes to impress them, which produces the opposite effect. I'll use the most horrible puns, the weirdest jokes, stupid hypothetical scenarios and sometimes absolutely goofy things just because it has become a habit. No one invites me out anymore because of this, I try too hard to be funny and act goofy which turns everybody off.

I don't know how to get out of this. This is a bad habit I've developed for years that prevents me from getting closer to everyone.

It might also be because at times I feel like the actual purpose of the conversation is to entertain and make the other person happy, because I feel like I have nothing else to offer them. So I seek that laughter to gauge if the conversation is going well. If I don't try stupid humor then I feel like they'll be bored.

Please help a fellow dude out haha. This has lost me 2 girls in the last week. Trying too hard to be funny and not to connect, and attraction went POOF.