Have you asked a friend to date?

I was friend with someone for many many years, he was my one of my good friends boss. We decided to go out to dinner together one night alone because my friend had a doctors appt and that was when everything changed in our relationship. It wasn’t that one made a move on the other I think it was mutual feelings we both felt when we were alone together.

I’ve done it twice. The first time was disastrous for the relationship. The second time was inconclusive, because he got outrageously busy with work (he bought a restaurant) and simply has no time to date.

Yes to the question. To the follow up question, VERY AWKWARDLY.

haha, I’m in the same boat as @mazingerz88

just steadily become more daring with whoever it is, get feedback first, and then go in for a kiss when the moment’s right

I was friends with a girl for 4 or 5 years before asking her out.
We dated for a few weeks, and she crushed my spirit and destroyed my ego.
Turned out a lot of the things she told me during our friendship were total lies.
We are friends again now, but I will never make that mistake with her again.