Dating Your Best Friend’s Ex – Should You?

This isn’t an easy one to answer and you’re going to need to do some soul searching. On the one hand you might lose a good friend, on the other hand you might lose the opportunity to date or have a relationship with the perfect girl.

We’re going to call the girl Holly, beautiful, ivory skin, and hair so dark and luxurious a guy could lose himself in the soft, sweet aroma. Holly was recovering from a breakout, she was a bit sad and lonely, and knowing what you do about women (you’ve read the book), you realize you could easily step into this situation and likely score gold.

Here’s the rub, the guy she broke up with your close friend. So what can we do, it’s catch-22, but  the clock is ticking and you know that someone is going to latch onto Holly, she too hot to be left waiting for long on the sidelines.

First thing to consider is how close your friendship is, does it go back years and years, or merely someone you’ve known for a short while. There’s going to be some tension, that’s simply life, the question is are you willing to put up with the drama to get the girl?

If he’s a close friend, my rule has always been to take a pass and move onto other, more easily harvested, pastures.   If he’s already dating someone else, then all bets are off and you can move in for the kill, or the consoling, take your pick, it’s likely to be some of each.

The one thing you MUST do is be honest with both your friend and the girl, and in this case anyway, the friend should be first. Simply find a time to buy him a beer and ask. I know it sounds easy, but when the moment comes, you’ll likely find a few butterflies, hey this is real life.

There always his side, her side, then the truth, so don’t ONLY listen to her (with the wrong head), but consider both sides of the equation. If possible, find out why the relationship ended, was their mistrust, cheating, or simply time for both of them to move on. If she dumped him and he’s grieving, c’mon, don’t pour salt on an open wound.

Take the time to look at the situation from both sides, if there are still emotions running high, you’d be wise to back off for a bit and stir the kettle. On the flip, if she’s the girl of your dreams stop dreaming about her and take action, which -as mentioned earlier- means you need to -man up- and be honest with both of them. This isn’t the time to be sneaking in the back door so your friend won’t spot you visiting his ex, there’s no future in that, unless all you want is a hot weekend, but then you’re likely not talking about the same level of friendship that I am.

As mentioned earlier, there will likely be some level of drama, know that going in and at the least you’ll be prepared for it.

Is she worth it? That’s a question you need to decide, think long and hard, you’ll make the right decision.

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