Dating A Friend's Ex-Boyfriend

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Dating a friend’s ex-boyfriend can be a tricky thing to do. If you handle it right, the three of you can remain friends. Handle it wrong and now someone’s gotta go. If you’re honest about your feelings for him to your girlfriend, she may very well be understanding when the subject comes up, especially if they broke up amicably. But if it was a bad break up, it’ll be messy.

No matter how the break up went, she may not want you dating her ex-boyfriend anyways. If you consider yourself to be her best friend, you should respect her wishes and steer clear of him. If you were the cause of the break up, keep doing what you’re doing. But, don’t be surprised when she doesn’t want to be friends anymore.

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If their break up happened months or even a year ago, talk to your friend about what you want. If the two of you can come to some understanding, maybe she she won’t mind you dating her ex. Every one is different and the two of you may be a better match than he and she were. Time will tell.

She will also see that you are respectful enough of her feelings to come to her and talk about this. She may be more agreeable to you two dating and having a relationship if she’s happy in her own relationship. Like I said, if the relationship just ended then steer clear for a while. Do not be the rebound relationship. They rarely ever work and then there is just more hurt to spread around. So, make sure their relationship is really over before jumping in.

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If your friend and her ex move in the same circles, you’re all bound to run into each other. This may get a little awkward. Right at the beginning, you may want to frequent different places until your relationship is on better footing. Then, start going to the places you always go. When you all run into each other, this should soften the blow somewhat.

Be aware of her feelings. When she does see you two together for the first time, she may feel a little jealous. Old feelings may come flooding back. Maybe some feelings she didn’t think she still had. Sometimes, it’s best to be discreet at first when dating a friend’s ex-boyfriend. After you’ve talked to her of course. Ultimately, you do want to take permission. But you also don’t want to be seen around with her ex so much that she thinks you’re rubbing it in.

Got something to say? Let us know in the comments below!

By Sarah Quinn

Sarah Quinn is a Make Him Yours XO contributor based in Oakland, CA.

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