Have you met this type of guy before? (quite specific behaviour case)?

I met this guy on a dating app, he is quite friendly and he invited me to go bowling and asked if i was competitive, he also mentioned that he wanted to buy me lunch/dinner. Everything here seems to be quite normal. He mentioned a bet and was like whoever loses wear his sneakers etc

On Insta: I have noticed that years ago he has had photos of other women wearing the same cap of his which to me is kinda weird but from recent he has not have any of those types of photos. This kinda made me worry that he may ask to take photos of me during our date or ask me to wear his things. (he did)

On the date: he turned up with a rose for me and he pretty much paid for the arcade, grabbing toy machines that he said he wanted to win me something, he also paid for bowling etc I tried to pay for drinks here and there to contribute but if we talking about finances it is ofc not equivalent. He went for hugs and possibly a kiss on the cheek but because i had a mask it was stopped and later in the day he did ask whether it was ok to? Within some time he did pull out his phone to take a photo of him and me but i had a mask on which he asked for me to take off for the photo. He also at the start asked me to wear that cap I was talking about but i indirectly declined but he said how about for photos at least? ( didn't happen) He was very flirty throughout the day and was like i want to look after you, he looks more like a nerd type so i wasn't sure whether his behaviour was just because awkwardness or he is actually experienced? During bowling he was insisting on the shoe swap which didn't end up as a bet like he mentioned. I wasn't sure but just went with it because i accepted the bet at the start so too late now. He also asked we should hold hands which i said maybe next time but he still grabbed my hand anyway.

What are your thoughts on this guy? (given some history and action) is this exhibiting player vibes? i don't want to sabotage but not sure? can explain about after the date!
Have you met this type of guy before? (quite specific behaviour case)?
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