I've always been the sort of person who can laugh at himself. Much of my humour is self-deprecating. I'm always the first to make fun of myself.

However, something I've noticed is that, while self-deprecating humour helps build rapport, disarms other people, and endears them to you, it only does so when it comes to making friends. When it comes to anything more than a platonic relationship, it really kills attraction.

It's likely because you're literally announcing to the other person, "I am not good enough for you." And if you're saying it yourself, why shouldn't they believe you?

It also probably comes off as needy. Self-deprecating humour is an ego-defense mechanism, ironically. The logic of it is that if you can make fun of yourself, it neutralizes other people's ability to harm you by making fun of you. Many people who were bullied end up adapting by being self-deprecating in order to neutralize bullies, and perhaps even win the bully's approval. It can also come off as fishing for compliments. "Maybe if I talk about how shit I am, the other person will feel sorry for me and try to convince me of how not-shit I am and try to make me feel better and will feel obligated to give me the attention and affection I want."

So, realizing all of the pitfalls of self-deprecating humour, my goal has been to, at least in the context of dating, eliminate it from my behaviour.

My issue, though: I don't seem to have anything to replace it with. All my life, I've been considered the "witty" and "funny" guy by people who've gotten to know me. But my favourite comedians being people who poke fun at themselves, like Conan O'Brien, the vast majority of my jokes have had me as their butt. This has gone over great with friends and acquaintances, but it turns off dates.

So, eliminating pretty much my entire schtick, I need fresh material. I always feel like a pompous asshole when I try to make fun of other people. A lot of rapport can be built when you and your audience make fun of the same target (say, you bond over how you both hate the kinds of people who post trite motivational quotes as their Facebook statuses), but I always feel mean-spirited when I engage in this, and I feel like I'm trying to build myself up by shitting on others.

So, how do I overcome my self-deprecating tendencies, and learn humour that doesn't diminish my value?