How do I tell this amazing guy how I feel about him?

As hard as it may seem, you have to be completely honest, I mean don’t go over board and freak him out or anything…. just tell him just what you posted here… about how you adore everything about him and that you had to take the chance and tell him! Worst thing that could happen is he will think your pretty adorable yourself just for thinking those things…I think things would work out just fine if you did this!

Do you think your friend’s parents would be ok with you asking him to your prom? If the two of you are in High school then it’s probably not a big deal, ask him to the dance- no need to spill your pent up feelings just yet. If he’s in Jr. High and you in High school then it might make him feel a little self conscious, that’s the only reason I can see where he’d say no unless he’s got a gf/bf already.

Don’t be shy baby… you can tell me anything.

I know it’s scary, but go for it. As a college-aged woman proud to be forward with guys, I regret the missed opportunities I had in high school because I was too shy to tell the guy how I felt. Now I never hesitate in making my feelings known, and as @amberrae suggested, the guys are usually impressed with my confidence. I get turned down, but I keep my cool and joke about it.

Here’s one idea:
At his house, go into his room or whatever.
You: Hi!
Him: Hi!
You: I have a couple messages for you.
Him: You do?
You: Yeah. First, [sister/friend] is wondering if she can borrow $10 for [something]. Also, she says to not forget to call Grandma. Lastly, ...um…I have a massive crush on you. I think you’re smart, funny, and super cute, and I simply adore everything about you. Oh, and your mom says to come set the table.

Rehearse, talk slow, and just get it out there. Feel free to change the subject before he has a chance to respond, if the suspense in the air is unbearable (as it usually is). I promise you can do it! You’ll be out of high school soon, and either you’ll have an amazing bf or you’ll be kicking yourself for eternity for not going for it. Even if it fails it will be a mere blemish on the scale of your life when it could instead be a highpoint.

Good luck, and keep us posted!!

P.S. I also tend to go after younger guys. I can tell you that you already have an advantage, because even if you weren’t totally awesome (which all Flutherites are) you’re older which is automatically hott. You being older will also give him the feeling that you chose him over a million other guys your own age, which is flattering. You definitely have the upper hand in this conquest. And if my own experience isn’t credential enough, I have a psychology degree as well :)

P.P.S. (Sorry, I’ll shut up after this:) never underestimate the age-old “have a friend tell him” technique made popular by 12-year-olds. Have your friend tell him, and if he believes her, maybe he’ll be bold enough to make the first move so you won’t have to! If he’s not into it, you can always pretend your friend made it up as a prank to both of you.

Ask a question about it in an internet forum.