Is It Ever Okay to Date Your Ex-Boyfriend's Friend?

Mike, 

I really need a guy's perspective on this. My boyfriend "John" and I went out for two years while we were in high school, and broke up a few weeks before we graduated. We now both go to different colleges--I stayed close to home, he went to a school a few states away. Here's the problem. My ex's really good friend "Tim" is at the same school as me, and we've been spending a lot of time together recently. We're really edging towards that "more than friends" territory. But I keep holding back because I feel that I'm breaking some sort of unwritten rule about dating my friend's ex.

I have no idea what my John would think if we did get together--we haven't talked since he left (no bad blood, I just felt there was no reason to stay in touch). Tim and John have been friends since junior high, but I get the feeling they're not that close anymore. I'm so confused. What do you think I should do? 
 

All rise for the case of “The Boy Friend”, Judge Mike Brown the REMIX presiding. (Forgive me, I always wanted to say that!!)  

So you’re thinking about dating ex’s best friend and you want my thoughts on the situation. Well if my ex dated my best friend, he wouldn’t be my best friend anymore, that’s it. But what would you have to lose? You two already broke up! Plus, you’re a woman with a mind of her own--date whomever you want to.  

Usually, the only rule is NEVER DATE YOUR EX’S FRIENDS. That’s if you never plan to get back with John. Why? Because by you dating John, then Tim, then John again, your high school reunion would have more drama than an MTV Reality Series. (Actually, it would be an MTV Reality Series.) But since you don’t even talk to John anymore, you have nothing to worry about. In this case, the ball is in Tim’s court. 

The unwritten rule you referred to is only for the fellas. And there’s plenty of rules, which are all encompassed under the almighty Man Law. All men are supposed to live life by these rules, which makes things even easier for you! Just tell Tim your reservations and listen to his responses. Did Tim and John's friendship last part Junior High? Does Tim even care?  

If nothing is resolved, he should refer to Man Law (as described by the general male Facebook population): 

“29. No man should ever hook up with his best friend's girl, no matter how hot she is. This is in effect while they are dating or "together." If they are separated, refer to Law 3 for the proper way to handle the situation. (Side Advice: Less guilt is involved if she comes on to you.) “ 

“3. If your best friend is dumped by a girl, it is a 6 month waiting period till she can be touched. If he breaks up with he,r it’s a 6 day waiting period. “ 

If things with Tim go beyond being friends, both of you could lose John So regardless of your plans, make sure to use your best judgment.  

Case dismissed.