O wise ones, I am in need of advice

Sorry to be the annoying girl fretting over a boy, but I am at a serious loss of what to do right now!  Ok, here is the scenario...bear with me .

I am 19 years old and have strong feelings towards my 24 year old friend.  We have worked togther for the past year and have always got along really well and we love to joke around.  This summer before I left, my last day of work with him (while trying not to cry, but not quite succeeding...) I told him to come visit me at school if he was ever in town (Coincidentely, I go to college in the place he grew up and family still lives).  We hugged and exchanged phone numbers.  A few weeks after I moved out, he started talking to me on facebook chat, and we would talk for hours.  He came to town for a 4 day weekend and we hung out everyday.  We went out to eat, to movies, drove around town, and he showed me the house he grew up and looked through his old yearbooks.  But nothing happened.  Over the next couple months, we will facebook chat all the time.  I don't think I've ever gone more than 3-4 days without talking to him.  Sometimes I'm frustrated because it seems like I am always the one initiating it.  Also, I would text him a lot (under the influence of alcohol, but never said anything bad other than 'i miss you')  Whenever I go home I text him and initiate a date.  We'll go out to dinner or a movie, and once I even went back to his place and watched tv.  I feel like we're becoming really good friends, we talk about a lot of stuff like past relationships and stuff.  He must know the way I feel, yet we've never even talked about whats going on between us.  Its so frustrating becasue these are so obviously dates, but neither of us acknowledge it.  It kills me, because I like him so much, but don't know how to tell him.  I'm so afraid of rejection and that he will not want to talk to me again.  I would think that if he didn't like me, he would avoid me or not initiate conversations online.  But, I just feel like he will never make the first move, and I think a lot of that may have to do with the age difference.  I don't know whether to hope this frienship will progress into something on its own, or confront him on the issue and risk our friendship.  If I could get some outside perspective on this, I would be forever grateful.  I have overanalyzed this to the point of insanity :-) 

It seems that while he likes you as a friend, he does not want to make it more. I'm only going by what you said yourself... you point out that "I would think that if he didn't like me, he would not initiate conversations online." And that's after you said "I am always the one initiating it". And you also seem to be the one initiating most of the dates.

It is a very hard thing to have to accept but it sounds clear that you feel more for him than he does for you. If a guy wants you as his girlfriend, he will come after you, especially with all the encouraging you have done. He's either interested in truly just being friends, or he is playing with you.

If there's one thing I've learned from the many relationships I've had it's that most men aren't telepathic, don't 'read between the lines' or notice subtleties.  If you hang around waiting until the penny drops you can wait a long, long time.   If there's another thing I've learned it's that 'platonic friendships' are almost non-existent.  In mixed-sex friendships, one person always feels something more than friendship for the other..... even if they deny it very hotly!

I say, tell him how you feel.  Best case scenario... you find out he feels the same way and all is hearts and flowers.  Worst case scenario... he thinks of you 'as a sister' (ouch) or he runs a mile.   Either way you know where you stand and you can move on accordingly.  If you say nothing you're just putting life on hold and wasting your time on a man who's not interested.  If you try to pretend someone's just your friend when you're really in love with them it's soul-destroying.  Because one day he'll send you a message on facebook about his beautiful new girlfriend and it'll break your heart.

Thank you so much for the replies :-)  I agree with both somehow.  I think that if by now nothing has happened, nothing will happen and I need to move on.  But I also know that the best relationships form out of good friendships.  He obviously likes spending time with me, so maybe I'll give it time.  But you're right, it really is soul-destroying to act like a friend and hide my true feelings.  I just don't know how to tell him how I feel.  Does anyone think that 24 to 19 is too big of an age difference?  I think we are at a similiar maturity level but sometime I think that hes afraid that he'll look like hes using me.

I don't think 19 and 24 is too much of an age difference, then again, if it were my daughter........ Tell him how you feel. If he doesn't feel the same, just lessen the frequency of you contact, but, continue a friendship on his terms.  Nineteen is very young and you have a lifetime ahead of you. There are certainly more fish in the sea and you don't want to waste your time on a minnow when there is a greater catch out there for you.  If he is interested, see where it goes and remember the above advice if it doesn't work out.  Good luck to you!

I'm 20 and my boyfriend is 25.  We began dating when I was 18 and he was 23.  My parents had no problem with the age difference, it is only almost 5 years (his birthday is in August, mine is in December).  My father is 62 and his wife his 42... so I don't think age has a whole lot to do with any thing once you are both of a mature age (ie- 14 and 25 would not be okay).

Yeah, maybe 19 and 24 isn't such a big difference.  I don't see it as a big problem, but maybe he does.  I think I do owe it to myself to tell him how I feel, so I can stop torturing myself.  I just need to figure out a way to say it.  I should definitely do it face to face right?  Thanks for the kind words everyone!