Here's one that will take a long time

[KnottedYet]

I am socially inept. Kinda like a guy. (but cuter ) If I had a crush on someone and they asked me on a date, I'd panic and say "no." (even though I wanted to say "yes")

So... maybe you shouldn't take "no" as an answer. Or maybe you should take the whole question out of the realm of words. (but slowly, so as not to frighten the timid wild creature)

[Tuckervill]

But don't put all your hopes in the one basket. It could ruin a beautiful friendship, if he perceived you as desperate--or more likely, made him terrified to hurt your feelings by saying no (most guys worth their salt are terrified to hurt someone's feelings and it could make him panic and avoid you for a long time). I wouldn't force a date on him, either, with the dressing up and all that.

Just bring it up in conversation. Be who you are. Be true to the relationship you've already built.

Karen

[KnottedYet]

Be true to the relationship you've already built.

Karen

Oh, Tuckervill, you are wise!

[Wahine]

Maybe you could convince him to take a bike touring weekend with you and just where things go?

[Starfish]

I wouldn't force a date on him, either, with the dressing up and all that.

I don't think you can force someone to go on a date, dress up or any other kind. You just ask, and they either go or they don't. It is up to them.

But, that really is what it comes down to...all you can do is ask for what you want, or make your feelings known one way or another (in a way that works for you), and then let go of the outcome.

And, as far as "ruining a friendship," the risk is either worth it to you or it isn't. You could lose or strain something you have now, and be sorry. You could gain something beautiful, and be contented. (ETA...or experience a gazillion other possible outcomes that you cannot predict.) Only you know where you currently fall on this spectrum of risk.

I really do wish you peacefulness. I know that when feelings are involved, these are not easy questions. <insert gentle smile>