Should I talk to him??

Hi, so I'm having a bit of a dilemma which I think is quite common but I'm not sure what is the best way of dealing it. So there is this guy in my sixth form who I think I like, I've known him for a while but have only recently felt like I like him more than a friend. I speak to him now and again but not properly. A couple of months ago he texted me and he sort of said 'hey how are you' etc. and we did have a conversation. However after a few late replies the convo ended. When I see him around sixth form we say hello, smile and sometimes have a bit of a chat but it always seems awkward when we're with our friends. The issue is, I don't know whether I should text him and say 'hey' without it being weird or out of my place. My friend said that I should but I don't know whether he might think it makes me seem desperate. I'd just love a chance to get to know him better because it could turn out that I don't actually like him because of his personality. A few of my friends are getting boyfriends now and it is amazing how happy they all are, and I just feel like I would be happier if I had someone like that (I'm aware this is super soppy omg ) - not that I don't have anything to be happy about because I do realise how lucky I am and I don't want people thinking I'm ungrateful, but I've never had a 'proper' relationship so I don't know how to go about it. Plus I have been close to about three other guys in the past and they're super nice and interested for a while but then they just start leading me on which has sort of knocked my confidence when it comes to guys:/
But what should I do? Thank you so so much!!!

Hi, so I'm having a bit of a dilemma which I think is quite common but I'm not sure what is the best way of dealing it. So there is this guy in my sixth form who I think I like, I've known him for a while but have only recently felt like I like him more than a friend. I speak to him now and again but not properly. A couple of months ago he texted me and he sort of said 'hey how are you' etc. and we did have a conversation. However after a few late replies the convo ended. When I see him around sixth form we say hello, smile and sometimes have a bit of a chat but it always seems awkward when we're with our friends. The issue is, I don't know whether I should text him and say 'hey' without it being weird or out of my place. My friend said that I should but I don't know whether he might think it makes me seem desperate. I'd just love a chance to get to know him better because it could turn out that I don't actually like him because of his personality. A few of my friends are getting boyfriends now and it is amazing how happy they all are, and I just feel like I would be happier if I had someone like that (I'm aware this is super soppy omg ) - not that I don't have anything to be happy about because I do realise how lucky I am and I don't want people thinking I'm ungrateful, but I've never had a 'proper' relationship so I don't know how to go about it. Plus I have been close to about three other guys in the past and they're super nice and interested for a while but then they just start leading me on which has sort of knocked my confidence when it comes to guys:/
But what should I do? Thank you so so much!!!