Guy's Behavior

How do I make a move on a really dense guy?

I have a crush on this guy at school. We became friends when the school year started, we've only known each other for around 4 months.
We went ice skating a few days ago (first time hanging out with him outside of school) with some friends. I tried to make some moves by sharing a hot chocolate with him and holding his hand while we skated, but it didn't really work.
After we finished ice skating, we all went towards the bus stop but my friends made sure to walk slower so I could be alone with him. He said he was tired and felt like passing out because ice skating tired him out and he didn't get enough sleep the day before, so I held his hand (idk I thought that would help him stay awake) all the way to the bus stop.
I made a bet with my friends that if I still liked him by Valentine's Day I'd ask him out, but I feel like we don't have any chances of being together. He also doesn't think romantically, he's always referred to me as a friend, and i'm very tired of it.
Our mutual friend said that it's probably because he's not confident enough in himself to think that any girl would like him. (he's really skinny, not that attractive compared to other guys at our school)
I like him because he makes the best memes and he cares about me (i was really upset once and he listened to me vent about my week). He asks me about my day all the time and is a good listener. He also is really hardworking (to the point where he gets stressed out about school and grades bc of his parents :( ) and has really pretty eyes.
He was also really excited when I got him a turtleneck for Christmas so that we could twin and wear the same thing. That was pretty cute.
I want to get close enough to him and make him more confident in himself, but I'm not really sure what to do. he's not the romantic type and he keeps friend zoning me.
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+1 y
I don't think I used the right word when I said that he's dense. Let me rephrase this:
This guy isn't exactly taking the hint on some of the things I'm doing but it's not like I'm being super forward about it to the point where he notices it.
I don't want to do anything he'd think is weird, and I don't know what those limits are either because I don't know what his past experiences were like.
I'm just trying to get closer to him. I don't want to ask him out yet.
How do I make a move on a really dense guy?
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