Read This Before Dating Your Best Friend’s Ex Boyfriend

Dating your best friend’s ex boyfriend can be a tricky and complicated situation. It’s a path that can be hard to navigate, but it can be done without sacrificing your friendship.

The Girl Code states that you should NEVER date your best friend’s ex. But, every rule has an exception. What if you and he develop a relationship many years after he and your bestie broke up? The rule just wouldn’t make sense then, right? But, what if your bestie tells you that she still has strong feelings for him despite having broken up years ago? What would you do then?

We know it’s tough and we understand your pain. So, if you’re in this boat now and you’re wondering how to sail the seas smoothly, here’s how you know when dating your best friend’s ex-boyfriend is a no and when it’s a go.

Dating your best friend’s ex-boyfriend is a NO when:

He cheated on your best friend.

young macho playboy handsome man in bed with three beautiful sexy woman

If his infidelity is the reason why their relationship came to an end, forget about the guy. If he cheated on your closest friend, who says he won’t do the same thing to you? You can’t prove that he’s a changed man. Lastly, cheaters are not worth losing a friend you’ve been with for years.

Their breakup was very recent.

Maybe you had a secret thing for this guy already even when he and your best friend were still together, and now that they parted ways, you think there’s a chance for the two of you.

While that may be possible, it’s important that you wait. Wait for your friend to heal and move on. You don’t want her thinking that you were just waiting for them to break up and, now that it has happened, you’ll jump on her ex-boyfriend without caring how that will make her feel.

Their breakup was messy.

A picture of lost flowers and a couple arguing in the background

If they didn’t part ways amicably, they may still have unresolved issues. They might get back together when things have settled down a bit or they might hate each other forever.

Whatever the situation, don’t date your best friend’s former man. If you do, you’ll just add insult to injury. At the very least, you should wait and see what happens to their relationship and then decide what to do.

She’s not over him yet.

You know your best friend is still is not over him when she reacts badly to the mention of his name. If remembering him pushes her to tears or makes her explode, it means the wounds are still fresh, so you should respect her and give her time to move on.

Remember that betrayal is not a nice thing to have to deal with and at its worse, it can be devastating.

Healthy friendships need help, understanding, and a generally positive environment.

It is essential to realize, identify, and recognize when your actions have a direct impact on her. if you don’t at least try to sympathize with what she is feeling, then are you really a good friend?

Actually, here are the things every best friend deserves!

Dating your best friend’s ex-boyfriend is a GO when:

Their breakup was mutual and there were no hard feelings.

Dating Your Best Friend's Ex Boyfriend

If they both decided to end the relationship because it was not working for them, and you know there aren’t any hard feelings between them, then it’s a good sign.

Your best friend may not mind if you date her ex-boyfriend. Just be sure to let her know about your intentions and see how she reacts. If she does not flip out on you, it’s a go!

It has been a long time since they broke up.

If it’s been several months or even a year since they went their separate ways, then you’ve probably waited enough time for your best friend to heal.

They remained friends after the breakup.

While people seldom stay friends with their former partners (it’s another tricky thing), if they’re both in other relationships and are now happy and content, your best friend may not care about you dating her ex-boyfriend.

This is the best situation and one where jealousy and awkward feelings rarely occur. So, go ahead and ask your bestie for her blessing.

She’s moved on from him.

Dating Your Best Friend's Ex Boyfriend

If your BFF is already in a committed relationship, one where you see that she’s happy and serious, that means she’s moved on. Talk to her and confide about how you feel; if she really is your best friend, she will understand your dilemma.

She will appreciate your honesty, having waited for the perfect time and respecting her situation. She’ll surely give you the green light to date her ex after your heart-to-heart talk.

Now that you have clear guidelines on when it’s alright to date your best friend’s ex-boyfriend, use your best judgment when making a decision. Always proceed with caution and love. We hope you not only get the guy but, more importantly, you keep your best friend’s friendship and love.

Have you ever loved an ex of your best friend? How did it go for you? Do you have any additional tips and advice for other women in this situation? Share your thoughts and words of wisdom in the comments!

And remember, some of us consider our friends as extended family. They have a big impact on our life. They are not only the ones we spend the majority of our time with, but they also have the most in-depth knowledge of us.

Although some friends use this information to undermine us, true friends use it to build us up.

About the author

Maine Belonio

Maine Belonio is a twenty-something mom and writer who has a penchant for coffee, long distance running, Tolkien, Switchfoot, and Jesus.

1 Comment

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  • If you really love your friend and don’t put your egoism above the friendship, you should be ok with that. If he is your ex you don’t have rights on him anymore. If this makes her happy, I wouldn’t prevent them.