My brother and I have this strict policy. We never date each other’s friends. We do so because we don’t want to have the other lose a good friend if the relationship goes sour. Because that’s what happened in the past when I dated one of my brother’s friends.

It was a bitter breakup and my brother became that shoulder for me to lean on when I was hurt, and my brother decided it was best not to continue the friendship because he didn’t want to physically hurt him for breaking my heart.

So I haven’t dated a friend of my brother’s since then. But I got a call from one of my brother’s friends on Sunday who is in town visiting family, and he’s asked me out to dinner while he’s in town. It would be fine if we were just going out as friends, but this is a guy whom both he and I were diggin’ on each other in the past, but never acted upon it because of the No Dating Friends clause that my brother and enforce.

And if we go to dinner and have a good time, I may want to see him again……and again……and again. This would all be perfect too, because my brother is out of town this week. He won’t find out about it, right? WRONG! The truth always has a way of coming out, no matter how you try to hide it. So my brother will find out about it at some point, especially if the guy and I want to keep seeing each other on a regular.

But what if that relationship turns sour? Will my brother lose that good friend like he did in the past? I would hate for that to ever occur again. There’s never an easy answer to to life’s questions when it comes to dating. What to do, oh what to do?