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!