Sit and think of the function of humor during the attraction process.
If you're able to pull off a completely orignal and witty line from time to time, people will see you as creative, smart. That's DHV without bragging. I've asked women what most turns them off about men when men first approach. A lot of women say bragging. We need ways to demonstrate value without having to point it out by bragging.
A second issue is to deflate a bad tension. Women are uptight about men "hitting on them". From what I can tell, that means they just don't like a guy pushing them faster or farther than they want. Most of us have had some girl "hitting on us", if we use the same definition of that phrase. It sucks, it feels creepy. Humor deflates that. Guys with a good sense of humor aren't viewed as pushy. Women are also uptight about men just playing games, that the men are not genuinely interested in the woman, that they just want quick sex, without respecting her. Women use tests in an attempt to expose this. Without denying your sexuality, humor makes you three dimensional. You aren't just killing time with her until she'll disrobe. You are honestly enjoying the moment with her. So, we have the tension of guys being too serious when they "hit on her", and guys not being serious enough by just going for a piece of a$$. Humor deflates this. You're a person, she can relax.
If you agree with this model, it points to how much humor is useful. You're showing value by being witty, creative. Peppering jokes is enough to make that point. Being a clown says you aren't being socially aware of showing interest in others, making connections, etc. Peppering also deflates the bad sexual tensions, her objections. But too much, well, you don't hear much of women having fantasies about Bozo.