Wednesday, November 18, 2009

Is It Ever OK to Date Your Ex's Friend?

I used to have a hard and fast rule: If I dated a guy, I'd never date his friend. Never, ever, ever in life. Wasn't going to happen. How dare the friend even try to holla.

But then one day, I found myself in a strange predicament. I dated a guy--we'll call him The Player--who was pretty much a jerk. He tended to talk down to women, and on top of that, he was a whore. He was not my boyfriend--so I use the term, "ex," loosely--but I did date him on and off for less than a year. On two separate occasions during that time period, two of The Player's friends told me that I was too good for him and then they each tried to holla at me. One was his best friend (I shot him down immediately). The other was a guy I'll call Mr. Serious.

I met Mr. Serious while out at a nightclub with a couple of my friends and The Player. At the end of the night, the guys offered to give me a ride to my car so I didn't have to walk by myself.

But here's the thing: The Player disappeared as we were walking to the car, and he wouldn't answer his cellphone. He left me alone with his two friends, who I'd just met that night. I assume that The Player went home with another woman that evening because he would not answer his cellphone when I tried to call to tell him that his friend, Mr. Serious, was trying to holla.

It was quite some time later, perhaps a year or so (when The Player and I were long since over), before Mr. Serious and I started seeing each other. But Mr. Serious is way into his job, like in a working from 7 a.m. to 9 p.m. kinda way. He is usually so tired that he's hard to be around at times. So things did not work out for us.

Then I saw him again this weekend, and now he's trying to holla again, in a very direct, no-holds-barred type of way.

He's hitting me with talk of wanting to be with me on a serious tip. He's asking me to give him another chance. Usually, I'd think he's full of it and would dismiss him without hesitation. But this is a guy who took care of me after I had surgery earlier this year (the last time we were dating). And even though he's a workaholic, he took off work to take me to a doctor's appointment that I couldn't drive myself to. Now you know that's saying a lot for a guy who barely leaves the office.

I am hesitant, though, but it's no longer because of The Player. It's because Mr. Serious is an over-the-top workaholic, and I'm not sure I can deal with that. Under most circumstances, I'd be fine with a man who works hard, but if you take your fatigue and stress out on me, it's a different story.

Still, it seems strange to me that the fact that I once dated The Player no longer seems to matter in my eyes when it comes to Mr. Serious. A male friend says that Mr. Serious broke "man code" by trying to talk to me, so he doesn't trust him. But I guess that just isn't a big deal to me. Maybe it's because it's been at least two years since The Player and I were involved. Or perhaps it's because The Player is such a dog that he just has no relevance in my life in a romantic way any longer. We're cool as friends, but that's about it. The question is: Should I give Mr. Serious a real chance? 

TALK BACK: Is it ever OK to date your ex's friend? Please vote in the poll!


  1. I don't agree with dating a friend of an ex in any circumstance. However, if you really want to give it a go with Mr. Serious you should be honest with him about your concerns. If he can address your concerns and provide you with what you need to make this work, you should proceed.

  2. It's weird. I used to feel the same way about dating a friend of a guy I used to date. Since then I've heard of people who married people they met through someone they used to now I'm not so sure.

    I don't know about Mr. Serious. The jury is still out on him. I think he cares but he takes himself so seriously that I just don't know if I can deal.

  3. It seems you have two pretty big issues to deal with in this situation. It may seem like the fact that you dated the Player shouldn't matter but it actually does matter a lot. Think about this for a second. You are considering seriously dating a man who went behind his friend's back and tried to date you while you were still dating his friend. This shows serious signs of deceit, disloyalty, and selfishness. This is a person who can turn on someone who he's known longer than you. What makes you think that he couldn't do something similar to you? Someone that he has only known for a fraction of the time. No matter how big of a dog his friend was or if he thought he was doing the right thing by putting on his red cape and playing Captain Save-A-Hoe, the bottom line is he went behind his friend's back. On the flip side, if The Player was that big of a dog, he may have given Mr. Serious the go ahead which opens a different can of worms. Either way it's not a good look.

    The second issue you should probably consider is his workaholic ways. From what you described, it sounds like he has a problem balancing and separating his work, social life, and his personal life. You made reference to signs that showed he could take his work frustrations out on you. If this was the primary reason you two didn't work out, the second time around might not be that much different. I'll say something here and this holds true for any man any woman.

    People do not change unless they make a serious conscious decision to do things different in their life and this realization doesn't usually come until they have had enough experiences that teaches them what they are currently doing isn't working and it's time try something different.

    With that being said, unless Mr. Serious has had some serious changes in his life or unless something has seriously changed at his place of work...chances are he is still the same. It it has been like 3 months and he is on some ol BS like, "Oh I'm different and I have changed" chances are it's just that...BS.

    Bottom line is, this dude has more red flags than a store that sells throwback Soviet Union flags. At the end of the day it's a matter of what you are willing or not willing to deal with.

  4. @Madd Real Love -- You sound like someone I know. :-) Honestly, Mr. Serious's chances are not good. He is too much of a workaholic and doesn't know how to manage his stress. I've been thinking about it for several days now and just can't get past that.

    To answer your question about how long ago it was...he and I stopped talking in February, and yes, it was because he's a workaholic and can't seem to manage his stress. He takes it out on other people.

  5. If you know anyone who sounds anything remotely close to should definitely listen to that person because they probably knows what they are talking about. ;)

    Seriously though, if you had someone in particular in mind, chances are I'm not that person.

  6. all depends what you had going with said "ex" and how close this "friend" of his really is to him.

    If you with said ex
    a. never had sex
    b. dated over 5 years ago

    If said friend is..
    a. not that close a friend
    b. doesn't know you through the ex

    then, I don't see the problem! :-)