Advice Needed: How Do You Make The Transition From Friends To More Than Friends?

I have stumbled upon a dating conundrum that I cannot figure out on my own. I don’t need to consult an advice columnist, or my friends or therapist. I need to hear from the people of the world at large who have been through this and have practical pearls of wisdom to bestow upon me.

So here’s the dilemma: The other night I was out with some friends … wait let me back up. Here’s what you should know: This dinner bunch is a tight circle of friends. We work in the same field and our bond is not only personal, it’s professional. One of the members of this group is a guy that has been a close friend of mine for the last two years. I have always sensed some attraction on both of our ends at different times throughout our friendship, but neither of us have ever acted on it at all. Never in any overt way, at least. Over the past couple of years, we’ve become really, really close, sharing stuff about our families, dating lives, professional lives and personal lives. This guy probably knows more about me than most of my closest friends.

Anyhow, back to dinner. Two of our friends took off and the third got up to use the restroom. That is when Guy Friend dropped it on me: “I am so attracted to you that I can’t look you in the eye. I’m having trouble breathing even saying this.” Then he grabbed my hand and said, “I love you.”

Now mind you, we tell each other we love each other regularly. I do this with all the friends in this group. He didn’t say he was in love with me. I didn’t really know what to say except, “I love you, too.” Which is totally true. I do love him.

After dinner, he planted one on me. All systems were a GO in the kiss department. We shared a kiss. That was it.

So, this is where it gets complicated. I have a couple of reservations about him. He has a history of pushing women away when they get close to him. I know this because we’ve talked about it extensively. I witnessed it in action with the last girl he dated. When he declared his feelings, or attraction, or whatever, he followed that up immediately by saying that he was afraid that he would hurt me or let me down in some way.

Besides both of our reservations, which we discussed, there are other things at stake here: Our friendship (which is really important to me), our group of friends (we all know how quickly things could get awkward if something goes wrong), our professional connection (I take my career seriously and so does he), and my heart (which I don’t want broken … I know, no one does).

When we had finished the kiss/discussion of reservations, we both had no idea what to do next. I know that on occasion, people go from being friends to more than friends.


“Maybe we should go on a date and see how it goes?” I suggested.

“But that’s so formal,” he said.

And then, this was the thing he said that stumped me: “We’re such great friends and I think we would be such a great couple, but I can’t figure out how we get from one to the other.”

That shut me up. I didn’t have a clue how to respond. Trust me, I have faced more than my fair share of dating dilemmas in my love life, and I’ve usually known (or at least been able to eventually figure out) how to handle them. But this is a new one. I’ve never been in this position before. The closest I’ve come is when I accidentally had sex with a guy friend of mine while drunk. It was awful and we didn’t talk for two years. This is way different. I am lost. Confused.

You have all the information now. Please advise.