I get this question a lot, or similar ones about how to ask or tell a guy something in a certain way without sounding another way or making him mad or scaring him off. I don't usually answer them because I don't usually know the answer. There's simply not enough information.

So much about these scenarios depends on the individuals involved, their personalities, their history together, and so many other factors. What works for one guy could easily send another guy screaming for the exit. Some guys value honesty and candor, while others feel like any mere mention of the thing you want--marriage, to be more than a friend, more sex, whatever--equates to nagging, and they resent it. It all depends on you. And him. And how the two of you are together.

In your case, I don't know if you'll sound desperate because I don't know if you are desperate. You don't sound it here, but who knows? I don't know how your guy will react because I don't know what he's like, what you're like, or how well you already communicate with each other. I don't know how you became friends, how long you have been friends, if you were ever more than friends, etc. You get the idea.

But you know what? None of these things really matters in the end. We already spend far too much time worrying about how we'll sound or how people will react. We think and rethink and second guess ourselves, then we contort and dilute and subvert our message until it sounds nothing like what we really wanted to say. When it fails, we don't know if it was the idea that failed or just the way we presented it. And then the second guessing starts anew, that is, if we have any energy left.

How someone will take us or react is largely out of our hands. Sure, you can target your message to your audience, but that works better for advertising than it does for human relationships. People hear what they want to hear. They react how they want to react. We need to let go of the illusion that we have control over their response.

My advice to you is this: tell him exactly what you want to tell him as honestly and openly as you know how. Speak from the heart, not the head, and put everything on the table. The words will come, but they won't be perfect, which makes the message even sweeter and more authentic.

How he reacts is ultimately up to him. If he rejects the idea of dating, so be it. You tried. Nothing ventured, nothing gained. If he's not into you like that, he's not into you like that. The result would probably have been the same no matter how you delivered the message. If nothing else, you'll have the satisfaction of knowing that you gave it your very best shot, your heart in your hands, with every bit of emotional honesty and candor you could summon.

Life is short. Seize the day. When you get older, you'll wish you had.

Best of luck. I hope things go your way.