Dear Bossip: I Met A Guy, But He's A Friend Of My Ex From Years Ago

Dear Bossip,

I have an issue going on. I met a guy at a restaurant a month ago.

He was sitting in a booth behind my ex-boyfriend. I immediately noticed the guy and whispered, “Damn, I should be sitting with you.” The guy replied for me to come and join him. After coming back into the restaurant to give my ex something for my son, I slipped the guy my number. He texted me that night, which was on a Saturday. He asked me out for drinks, but I refused (I don’t drink). I was tired so I asked him if we could reschedule.

The following week I rarely heard from him. Then, he comes back into town and sends me a text that he was in town. Next, he proceeds to tell me via text that he knows my ex and they worked together back in the day and actually were roommates! I was disappointed, but not surprised.

So, that evening we met up to talk about it some more. They were friends in the early 90s. He wasn’t aware my ex was sitting right behind him in the restaurant until my ex got ready to leave. So, we actually had a really nice time that evening. The following day we caught a midnight movie and a bite to eat afterwards.

I am turned on by this guy. I’m just confused as to what to do. I don’t know if he caught the vapors when he saw what kind of car I drove or if he is getting a thrill out of f**king his old homeboys son’s mother. We have more in common than my ex! What do I do? They hung out 20 years ago. My relationship with my ex was bad. I’m so confused, and even though he was an abusive a*#hole, it still would hurt me if he found out. But, on the other hand what if this situation is right for me? I deserve happiness too. What should I do? – Confused In NC

Dear Ms. Confused In NC,

Do you want love and happiness, or do you stop dating all together and live a life in solitude because the chances of running into someone your ex knows, is friends with, or worked with will prevent you from dating?

You can move to another state so you won’t have to worry about running into someone your ex knows. Therefore, you won’t be confused, and you wouldn’t feel hurt for dating someone your ex knows.

Which leads me to my question – Why do you care if your ex finds out if you’re dating someone he knows? Do you still hold some love, or feelings for him? You said he treated you wrong and was an abusive a**hole. So, he f***ed up and didn’t treat you right. You’ve met a guy who is really nice to you, and someone you get along with, and you have a lot in common. Unfortunately, they were once roommates, were once friends, and worked together.

Well, obviously they are not that close as friends any longer if he was sitting directly behind him in the same restaurant, and didn’t recognize him, well, not until your ex was leaving. However, it’s obvious they aren’t that close now. They were friends in the 90s and have moved on with their lives. Hell, if they were still friends and were close don’t you think he would have known who you were, or at least heard about you.

So, ask him if your ex ever mentioned you to him. Ask him if he knew you and your ex had a child together. Ask him if he knew anything about your relationship.

Look, I know it is awkward and some would say you don’t mess with your ex’s homeboy. However, they were friends in the early 90s, and obviously they are not that close any longer. If they were still the best of friends, then I would say HELL NO! But, it’s been over two decades and they’ve moved on with their lives, though they are still friendly, and you and your ex are no longer together. You meet a great guy and it turns out he knows your ex. I wouldn’t rule out that you continue dating, and getting to know one another. Simply take it slow, see where his head is, and what his motivations are, and his real intentions.

If he caught the vapors because of the type of car you drive, then that will be revealed rather quickly. And, if he keeps pressuring to sleep with you, then, of course that is another red flag. So, take it slow. Date. Have fun. Enjoy yourself. Get to know one another. It seems pretty early and you are still getting to know one another. He can be telling you anything. However, I do appreciate the fact that he was honest about his friendship with your ex. That says a lot about his character. He could have said nothing, and led you on and slept with you and then revealed to you about their friendship. But, he was upfront and honest. Take note of that.

Look, you are grown folks. You’re not little kids, and hopefully you can handle this as mature adults. The other thing you have to consider is your child that you have with your ex. If you and he grow into something more than friends, then, your ex will have to be comfortable with knowing his friend is someone who will eventually meet your child. Again, if you are grown a** adults who can talk these things out and be mature about the situation, then, he should be happy that his friend, someone he knows and possibly trusts is in his child’s life.

At the end of the day, you deserve happiness. You deserve love. You deserve to be with someone who will love you and your child. If this man is someone you enjoy being with, spending time with, and you grow into something more, then you can’t prevent that from happening. You can live the rest of your life not dating or avoiding folks because they may know your ex. Who has time for all of that, and, especially dating someone he doesn’t know only to appease him! Girl, get your life, and do you. Hell, if the shoe was on the other foot, and he had met one of your female friends he wouldn’t stop dating her or seeing her because you and her were once friends. He would be doing him, and not even thinking about you. – Terrance Dean

Hey Bossip Fam, what do you think? Share your opinions and thoughts below! Also, e-mail all your questions Terrance Dean:  loveandrelationships@bossip.com  Follow Terrance Dean on Twitter:  @terrancedean and “LIKE” Terrance Dean on Facebook, click HERE!

Make sure to order my books Mogul: A Novel (Atria Books – June 2011; $15); Hiding In Hip Hop (Atria Books – June 2008); and Straight From Your Gay Best Friend – The Straight Up Truth About Relationships, Love, And Having A Fabulous Life (Agate/Bolden Books – November 2010; $15). They are available in bookstores everywhere, and on Amazon, click HERE!