What does it mean when a guy likes girls who "make him laugh and challenge him"?

I've recently starting seeing someone I met online and I like him a lot. However, he doesn't feel the same attraction/chemistry/sparks toward me which sucks. From what I've heard, he used to date someone who's "hilarious, witty, sarcastic, and made him laugh a lot" and he said girls who "make him laugh and challenge him" are two qualities he easily falls for. I asked him what he meant by someone "challenging" him and he said he likes being made fun of playfully, or someone calling him out, etc. I feel like when I'm with him I'm pretty relaxed and we always have a great conversation, but I guess I make him smile and not laugh that much. But how do I figure out that line between really funny and going overboard/judgmental, though?

On the other hand I feel like I'm not given a fair chance here since we met each other online and when we go out on dates we're literally strangers still getting to each other from the basics. People are naturally more polite or reserved and don't know what jokes/comments might offend the other person so we're more careful, unlike with someone you've known for a while in real life. So I just wonder if this type of chemistry that he wants can grow over time.

And another mystery is that although he seems like he's not over his ex (who happens to be his coworker whom he sees everyday) yet, and that he's not that interested in me, he hasn't expressed his intention to end our dating to move on to someone else. Overall it just seems like he wants to continue but is giving only halfass effort here...

Also, he seems like a quiet and polite guy himself with a nerdy side so I wonder maybe that's why his world is always rocked by someone more crazy and colorful...


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  • Sounds like you are a rebound. Sorry mate but it really sounds like he still likes his ex.
    To answer your question a person with a unique personality. Like me :)

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