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Dating a Friend's Ex-Girlfriend: How You Can Do It the Right Way

He wants to date his friend's ex-girlfriend

Should you date a friend’s ex-girlfriend? Is it ever the right thing to do? If so, how should you go about it? All of these questions will be answered in the guide below.

Please bear in mind that this is the gentleman’s guide to dating a friend’s ex-girlfriend. If you couldn’t care less about hurting other people’s feelings, go do whatever you want and find a way to deal with the aftermath.

In this guide, however, the aim is to show you how to date someone so that the nasty repercussions are minimized.

With that said, let’s dive straight into it.

How to Start Off Dating a Friend's Ex-girlfriend

If you’re taking the time to read this guide, it’s probably safe to assume that it’s a close friend who used to date this woman. If it’s anyone who you ever want to hang out with again, you need to ask him if it’s OK to fool around with his ex.

It’s the non-scumbag thing to do.

If you’re planning on only fooling around, there’s an argument that you could get away with it without him finding out. But someone could find out and tell him. She could tell him.

There’s also an argument that it’s not worth jeopardizing a solid friendship for some meaningless bedroom action.

Whatever your intentions are, the gentlemanly thing to do is to ask your buddy if he’s OK with it happening. Even if you’re sure he would probably say yes anyway…

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How should you ask your friend to date his ex-girlfriend?

You want to focus on the fact that there are feelings you are sharing for each other. Make it clear that there might be an exciting emotional connection blossoming - and that’s why you want to pursue it.

A real connection is hard to find, after all.

But, of course, you wanted to know how he’d feel about it before you proceed. Because you’d hate to do anything to ruin the friendship…

If you make all of these points, there’s a great chance he’ll do the honorable thing and stand aside for you.

But what if there are no feelings - and you’re just horny?

Now, that’s an interesting question, isn’t it?

Would you feel a bit strange asking for permission in that situation? Does it feel more like he might say no? And why is that?

Could it be because meaningless casual sex isn’t hard to find? Or it shouldn’t be if you’ve got your life together, anyway...

So, why would you risk disturbing a friendship for something that most guys should have no problem getting??

This brings us to the main point of this article...

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What kind of guys consider dating a friend's ex-girlfriend like this?

Yes, there are situations where a man and a woman discover a unique and beautiful emotional connection before they even begin to date or get physical…

But there are other scenarios where a man ends up sleeping with his buddy’s ex-girlfriend, which are arguably more common.

  • He’s a selfish scumbag.
  • He’s a sex addict.
  • His sex life is so scarce that he’d throw his friend’s feelings in the gutter just for a piece of ass.

If you feel guilty about asking for your friend’s permission, there’s a good chance that you need to work on fixing one of these three problems. In this case, if your friend has any feelings remaining towards this woman, he has every right to not want her anywhere near you.

Is she just trying to make you jealous?

If this woman isn’t over your friend yet, there’s a chance she’s just targeting you to get back at him. And a clear sign this woman is bad news. This is something else for you to look out for - and, of course, avoid.

What if your friend says NO?

Let’s assume you asked respectfully and led with your emotions as advised above, and he still didn’t want you dating his ex.

This is where your conscience really comes into play…

Do you understand why he denied your request, or do you now think that he’s the selfish friend?

The answer will surely depend on how serious his relationship was with her, and how long ago it finished.

If you thought the relationship wasn’t a big deal to him anymore, let him know. Perhaps he’ll explain that he still has feelings towards her.

If you’re not convinced by his explanation - and still think he’s being an asshole for trying to deny you - perhaps you may decide to still pursue things with this woman anyway.

That’s your prerogative. The friendship may still be jeopardized, but you may believe that he’s the one jeopardizing it now.

Your mutual friends may see it the same way, especially if it emerges that you and this woman really do have strong feelings for each other. This is an important point that will be explained further in this article’s conclusion.

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What are the potential consequences of dating her?

The most obvious consequence of pursuing this relationship is that it may permanently ruin your friendship. If you’re not willing to risk that at all, don’t lay a hand on this woman without your buddy’s permission.

However, there are potentially deeper repercussions of dating your friend’s ex, even if you ask respectfully beforehand.

If you share mutual friends with this guy, it could cause a rift in your friendship with them too. Most likely, he will explain why he thinks you’re a scumbag and try to turn them against you.

The only thing you can do in this situation is explain the steps you took to respectfully ask for his permission before making a move, and how it was clear that he should be over the breakup by now.

If you honestly believe you were right to proceed with this woman, there’s every chance your mutual friends will feel the same. And perhaps your old friend will eventually see the error of his ways as well...


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