So this guy has asked me to go places with his family a few times, and more recently he has asked me to "hang out" alone with him. He recently asked to go on our fourth "date", but he never calls them dates, just says something along the lines of "do you want to do something next week." However, one of our dates was on Valentine's Day and he did send me chocolates and a note saying I was "stunning". He is very shy and awkward (as I am myself haha) and he hasn't initiated any physical contact, but I have hugged him and held hands with him (as an excuse for helping him ice skate haha). But we just act very "friend-like" on the dates, so I always feel like he doesn't like me as more than friends, even though I'm pretty sure he does. Oh, and we also went to prom last year, so I guess that counts as another date. Any advice for my situation?
And I have not had been in a relationship before or anything like that, so I have no experience with guys haha. We're both in college.
It sounds like he likes you! Usually I won't introduce a girl let alone take her somewhere with my family unless I like her! Shy guys like him enjoy doing things with you and have such a great respect for you they will not make the next step forward of being more than friends until you do! lol this sounds like so many friends of mine and because the dudes were too shy to go further into the relationship it ended... So make a move ;) even if it physical contact feels awkward he problem enjoys it.
Yeah, sounds like he's into you pretty deep (*cough*). Hell, if I did that, it would be because I'm romantically interested. Very shy, for sure. It may take ages for a shy guy to confess his feelings to you, so this is when he'll be needing your help.
You don't have to say anything. Just smile and keep charming him with constant eye contact. Lots of hugging and sharing secret. Some romantic relationships start without either side having to say anything.
It kinda sounds like he's too shy to confess anything with words. That's probably why he's been trying to show you with his actions. I don't know any guys who would legit send a girl chocolates and call her "stunning" without being even slightly interested in her. And you said yourself that he's shy and awkward, which makes it even more obvious. I don't think he'd go out of his way to do something like that for someone he wouldn't consider special.
The best thing you could do in this situation is probably just confess about your own feelings, especially if you're less shy than him. He's going to need so much more time to build up the courage to do so himself. And if he's too shy, chances are he might not even do it at all. That's pretty much why you probably should take the first step. He's probably just as confused as you, and doesn't want to risk getting hurt just in case you don't feel the same for him. Talk to him!