Hi Damon,

My name is Tiffani, My question is…… My friend and I been friends for twenty years. I have always have romantic feelings for him up until now,he recently ended his relationship. Lately,our relationship have been more than friends. At first I was happy I had no worries but now I’m fearful. I guess, this is stemming from my own insecurities and over thinking. I wanted to know how can I overcome my own self doubt about our relationship. He is a great guy and he have a lot of qualities I want in a man. And how can I be supportive during his break up.

Tiffani,

You know how they say that with each experience is a lesson and if you have yet to learn from an experience than you are bound to repeat it again? Well consider me repeating a grade.

You know how it goes: Girl meets Boy, who appears to have all the qualities in a potential mate.  Girl and Boy calls, text and hang out to get to know one another. Girl likes boy and girl thinks Boy likes her too.  However, after a few months of great conversation and casual flirtation, Girl is wondering why Boy hasn’t advanced the relationship any further. So Girl puts on her woman pants and ask Boy if this attraction is mutual.  Boy, flattered (so he says) tells Girl that while he thinks she is cute and great, he is just not emotionally ready for a serious relationship. Instead, Boy just wants to be friends with said Girl.

Ahhhh yes, the dreaded “friends” zone.  A horrible phrase used, in most cases, to cover a wide range of meanings and offer just as much confusion.  See, this is my bad. I have been here before -more times than I care to have been or even admit. I should have learned by now to never become emotionally exclusive with a dude before he fully commits.  But I got the lesson now and hopefully, I won’t be bound to repeat it again.

But what do I do now that I have put all this energy into building this great rapport with this guy, who despite his lack of interest in a relationship is not a bad dude? I mean, we have lots in common and get along great. Perhaps by being his friend, he’ll one day come around and change the way he looks at our situation, right?  Wrong.

I know that somewhere deep down inside of us, we think that if we stick long enough with a decent guy, who says that he is not ready for a relationship, and provide for him the compassion, understanding and in some cases, physical affection he needs, he will turn around and profess his love. Just like in the movies.  But real life is not a fairytale script starring Sanaa Lathan and Taye Diggs.  And one of the lessons I was taught many, many bad “friendships” ago was that once he has defined his relationship with you, no amount of nursing would change that.

Would you ever consider dating your friend’s ex? Would you do it under certain circumstances? See what these New Yorkers had to say about it!