When and how should I tell him?

I've been friends with a guy whom I met online, lets just say his name is "John" and there's a 16 1/2 year difference between us I'm 19 and he just turned 37 last month. We've known each other for about 5 months now and over that period of time I started developing such deep feelings for him. I mean when I come out there on his day off, he gives me kisses out of nowhere, holds my hand in the car while he's driving and holds me when we take short afternoon naps before it was time for me to go. I'm really confused with where I stand in his life. Everyday he would call me 4 - 5x a day just to see how I'm doing and to let me know where he's going/what he's doing and when gets off from work he would call me and tells me how his night at work went and also ask how my night was.

I remember sometime about a couple of weeks ago he had told me that a co-worker of his had asked him why he's still single and he said to me that it takes him 6 months to get to know a person and to finally make that move. I didnt really ask who this lucky person was but I sometimes I wish I should've. I'm not sure if that lucky person was me because I'm the only person he spends his days off with ever since I met him. He doesnt have that much friends at all and our activities ranges from having lunch, going to the doggy park, going for a hike, thrift store shopping or maybe just a drive around the city.

I ask myself over and over again if I should wait until that 6th month which is the 14th of May. What do you think? is 6 month enough time to make that move?

Are you asking when you should make a move? i wasn't sure of the question... Seems like you guys are on a good path now... Friendship first lovers next... defintaly a plus... If you want to share your feelings and tell him then why wait tell him!!!

14th of May is not so far, but I don't think you have to stick with dates. If you feel the need to speak about it, I think you can do it even now. It looks like a healthy relationship and I would expect him to welcome any of your thoughts and expressing feelings.

Not to be rude but this sounds very high school:

"He says he likes someone and I don't know who it is, and it might be me but I'm afraid to ask..."

Come on. You spend all kinds of time together. You just haven't had "the talk" yet. If that means he isn't sure about you yet, well... he should be old enough to know.

not high school at all.

He once told me that he likes me but it's my age that scares him. But if I was to tell him my true feelings and just rejects me, I think it would be best for me to move on without him in my life because even if I was to accept things on a friendship level -- it'll hurt me even more knowing he already knows about my true feelings for him.

ok, so why don't you ask him to reveal his feelings?