Sense of humor

I’ve been dating this guy for a little over a month and am feeling some resistance when he says certain things. For the below example, I don’t think he’s funny. We actually had this exact same conversation last week when he told me he won $1100 gambling, and I told him that was impressive. He says I should quit my business and go pro – then he said it again this week. What does he want to hear from me? I don’t find the conversation interesting, funny, or even entertaining t me, it feels like useless filler words and I am bored by it.

C: X says “I should sell my business and go pro lol” (he means professionally gamble on sports)
T: I want to be with somebody has a similar sense of humor to me, and X does not have that
F: Resistance
A: I respond “I think we already discussed this and decided it was a bad idea” with a little silly smiley face. I talk to my friend about it. I write on ask a coach. I don’t look for somebody who has a similar sense of humor to mine. I see differences in X and I instead of similarities. I think about all the other people who I have found funny.
R: I have no idea what my result is. I know I’m supposed to look at what I create for myself, I think I was honest without being mean.

I have no idea how long I am supposed to be with this person until I feel like he’s not for me. I’ve given myself a tentative idea in my mind that I’m going to continue through Christmas, but – then what? I don’t know how to feel CERTAIN that is either is, or is not for me. We have so many other things in common that are “nice”, but it definitely still feels like something’s missing. I don’t feel “lit up” by him, I feel completely flat and neutral.

Any insight is very appreciated.