I’d sat across from my friend Kevin at restaurants before, many times, to eat and enjoy his company.

This time, I was nervous. This time, it was a date.

He’s the one I talk to about guys, the sounding board. He’s one of many good friends whose presence helped me after my last breakup. Knowing I have such great people in my life makes me feel lucky, makes me feel like I can conquer the world if I choose to.

Out of nowhere last week, he called to ask me out on a date, knowing full well I already had a date lined up with Craig. Major kudos for that. Must’ve taken some serious guts.

So we sat across from each other and had yet another great conversation, as always. And as we talked, I looked at him. Could I consider this man more than a friend?

I won’t lie. The thought had crossed my mind many times. He’s attractive. But something always kept me from walking down that road.

I place a high value on friends. When you live far away from your family your friends become your family, the people who care, who know the nitty gritty daily grind shitty awesome wild weird details of your existence on this planet.

Once the line is crossed, can you go back? If/when we broke up, would I lose him and my other amazing friends in that group in the bitter breakup backwash?

Besides, I’m having FUN right now. I’ve never been single in Raleigh and I love the blissful freedom. I’ve rarely felt so young and alive and in control of my destiny.

I expressed those concerns during our date, and he understands. So that has me thinking, becoming friends with someone before you date them is a good way to start. At least the lines of communication are open. Chances are, you have things in common. You already know a lot about that person, his baggage, quirks. Would it be so bad to cross the line, stepping out of the comfort of friendship into new territory?

The truth is, I would chuck all my worried-about-the-friendship bullshit out the window if I thought he and I were meant to be. I think deep down I’m just chicken. Too chicken to admit that if I really felt strongly about him as more than a friend, I would have done something about it by now.

Wouldn’t I?

Have you ever dated a friend? What were the challenges and advantages?