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Rules for Dating your Friend’s Ex-Girlfriend

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So your good friend was dating a total hottie, and she gave you a few hard looks when you were introduced. You gave her a comprehensive glance up and down, and decided your friend was one lucky son of a gun.

Alas, things didn’t work out for your friend, and he split with the hottie. Ever the opportunist, you’re thinking how she checked you out, and that maybe you have a chance to get in this girl’s pants. But what about your friend?

Can you really date your friend's ex?There are certain rules of Man Etiquette in this situation which you must follow, unless you want to end up on the receiving end of a sucker punch to the nose. Chicks are fun, but you don’t want to risk your friendship. It’d be bad enough to lose your beer-chugging chum, but if you go behind his back you could piss off all your poker buddies.

The first thing you need to do is assess the situation. You’ll need to know how long their relationship was and who initiated the break-up. If your buddy was dumped, then you’re treading on thin ice going after this girl. I hope she’s worth it.

If you’re buddy was upset by the situation, you might want to lay off for a while. Chances are he might tell you, “Sure, you can date that bitch. I don’t care.” But he might be lying, and if she doesn’t screw you over he might hold it against you. If she does screw you over… well, then you get screwed over and he laughs and says, ‘I told you so.”

Neither of these is a particularly perky situation for you. So if he came out on the short end of the relationship, you can’t necessarily even trust his blessing for you to give her a shot. There’s also the chance she just shoots you down outright, and you feel like a total ass.

It’s like walking into the bear trap your friend just got out of… by chopping off his foot just above the ankle. Now you’re the imbecile stuck in the same trap. Soon there will be two bleeding buffoons hobbling along on one foot.

Now, on the other hand, if your buddy initiated the break up with said hottie, then you might just be in business. This is the situation where you can ask his blessing. Be sure he’s going to tell you all the terrible things about her, because even though he may be done with her, deep down he probably doesn’t want you all over her either.

Even though he may be predisposed to highlight her lowlights in such a situation, you should still hear him out. He may have some valuable information about her. Chances are he’s had a look at her patient file at the local STD clinic, and he might be able to save you from a world of hurt.

I’m going to guess that if she’s that smoking hot you’re not going to heed any of his advice no matter how appropriate it may be. You’re just going to don your leisure suit and turn on Smooth Operator… or whatever the kids are doing these days. If it involves a leopard print thong, I don’t want to know.

Look out for Miss Take Jenna...

Here’s the rub. There’s always a high probability that this girl is going to react in one of two ways. One, she may associate you with that cretin who dumped her, and want nothing to do with you. Two, she may associate you with that cretin who dumped her and want to use you to fuck him over as hard as possible.

The first one gets you a quick cold shoulder, and that’s fine. I’m sure you can take it. The second might get you a really freaky porno tape where you’re the star. Who can tell?

My point is to be wary in this situation. The best thing would be to just let her go. But I’m a guy too, and I know you just can’t do it.

The real key is that you need to maintain open and honest communication with your friend so he knows that what you do is done out of pure testosterone, and not intended to bruise his ego.

I personally have managed to maintain a healthy friendship with a guy whose girlfriend I entertained on a few select occasions. He was less than pleased, but we were able to laugh about it. I will mention that within a year he had returned the favor by diddling my girlfriend. Once he even got her into bed on the same night she’d slept with me.
 
Now how could I be angry at such an amusing turn of events? Well, not everyone is quite so self-secure or able to laugh at themselves. So watch your back when that happens.

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