Should you date your friend's ex-girlfriend?

What are the pros and cons of hooking up with your friend's ex-GF?

If you're thinking about dating a friend's ex-girlfriend, you should take a moment to consider some of the possible problems you may encounter.

To begin with, when we say "A friend's ex-girlfriend” we're not talking about someone that your friend dated for two weeks in high school 10 years ago. We're talking about a woman that he had a relatively serious relationship with in the last couple of years. It doesn't matter if your friend was the one who broke it off, or if he’s now in a perfect relationship with another woman. It's still a hornet's nest of potential problems that may leave you with a nasty emotional sting.

How about if he only dated her for a couple of weeks, or had a one night stand with her? It really depends on your friend. The simple truth is that some guys can handle it and some absolutely cannot, so you need to tread carefully if you value your friendship.

Perhaps your friend might be man enough to give you his blessing, but would he truly mean it? It's hard to say. Unfortunately, the only way you’re really going find out is to go ahead and date his ex-girlfriend and see what happens. When your friend sees that you are sexing his ex, anything he’d said to you before about it being ‘okay’ could go right out the window.

What you really need to do in these situations is be completely honest with yourself. Why do you really want to date this woman? Is it because you're comfortable with her, or is it because you fear putting yourself out there to meet a new woman like most guys do? If it’s the latter, doesn't that make you sound like a scared wuss? Aren’t you a better man than to live your life being afraid of women you don’t know?

Sure, it’s comfortable and easy to date someone your familiar with because you know what to expect. But how much fun is that? How much of man will that make you feel like in the end? The truth is, with very little effort you could be dating someone totally new and having the time of your life getting to know her better, without any possible relationship repercussions with a close buddy. Doesn't that sound like a much better plan?

When you meet new women (who haven’t already been sexed by your friends) there won’t be any awkwardness in any of your relationships. Your friends will also be much more impressed that you’ve snagged a new woman outside of the safety of the ‘social circle’. If you need to learn how to talk to women, check out The Ultimate Guide to Conversation.

Picture this scenario: You decide to go ahead and date your friend’s ex-girlfriend, regardless of the problems it might cause. Then, one night you all decide to go out to dinner, or catch up for a drink. How are you going to feel when your friend and your new girlfriend (his ex) bring up conversations that start with, "Remember the time when we…"?

This is where something called ‘contrast’ kicks in. If the relationship that you are having with her is not as good as the one they had, or if he behaves in a more attractive way than you (i.e. more confident, funny, masculine) she will naturally compare you to him and reconsider her feelings for you. Does any of that really sound appealing?

Finally, what will you do if you and this woman break up? Not only may you have to deal with the pain of losing her, but you could have risked losing (or maybe have already have lost) one of your good friends as well. In a perfect world, you would get to maintain your relationship with your friend and keep the girl. Unfortunately, when human emotions are involved – things can get messy.

So, now that you understand all of the potential problems of this situation, what do you think when you ask yourself, "Should I date my friend's ex-girlfriend?" If you're the smart guy we know you are, the answer will be a resounding, "No!"

Do what a growing number of brave men from around the world are doing: Learn how to be confident, outgoing and attractive to women. Give yourself the lifetime gift of choice with women. Don't settle for scraps and don't cower away from being the man you want to be.