Search Results: valentine''s day plans

I'll start off with my question and then get into the details of our friendship. Should I tell my best friend Jake* that I like him and do you think he likes me?
Jake and I have been friends since middle school. In my home town it's kinda rare for a white boy to be such close friends a tall black girl, but we like defying norms. I never thought of him as a guy until he finally got a girlfriend in high school. She was horrible always talking about his weight and trying to push him into doing things that just weren't him. His mother used to joke that I was his girlfriend soon to be fiance to his grandparents, because that girl was so bad. It also didn't help that Jake was really popular with girls at our school. He always used to ask me why girls liked him and so I never had the guts to tell him I did. Then, when we graduated high school a group of us went to the beach and he started acting really strange. If I was talking to a guy he'd come up behind me and hug me or if I were sitting he'd touch my arm. I struggled a lot with my feelings for him then.
More recently, when I introduced him to my college friends he'd tell them I'm his girlfriend. One time he wanted me to tell everyone in the room that we dated, and if I didn't I was 'ashamed of him'. For Valentine's day, we had a whole day planned out with a movie and dinner. But the closer we got to the day he got more... snappy and anxious. I ended up not going because of weather.
The point of all this is to help you understand where I'm coming from. I just can't get a read on him.