Relationships, Uncategorized
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Reader Submission: Dating Your Friend’s Ex

I was wondering what your take is on dating your friend’s ex . For example, if your friend is happily married, and you run into her ex from 5 years ago, is it okay to date him?


Hmmmm. I think it depends. Although your friend has moved on and is married, when you’re considering dating her ex it’s all based on principle. Therefore, I would talk to your friend first before pursuing anything with the ex.

Now, approaching your friend about dating an ex can be a very sticky situation, so tread lightly. If you know your friend gets upset easily, maybe you already have your answer and shouldn’t date this guy because her feelings will be hurt. However, if your friend has tough skin let her know from the jump that you don’t want your decision to harm your friendship and this relationship is promising enough to have this discussion. Maybe everyone can laugh about this whole situation years from now like an episode of Friends.

Note: this guy needs to be spectacular! I mean taking you out, paying for meals, texting you in the morning and at night, calling to see how your day is going, praying for you, making you feel beautiful all the time, etc. If he doesn’t do these things then lets just end the conversation here because if this man isn’t someone you see yourself with in the long run, then what’s the point of risking a friendship?

Be prepared for your friend to be against the two of you dating, because I sure would be.  That has nothing to do with lingering feelings or any type of jealousy, but to me its just weird. I personally wouldn’t want to see my ex at my birthday celebrations or holiday parties when you bring him along as a plus one. Sure, you could leave him at home, but do you really want to spend an entire relationship tip-toeing through socially acceptable situations? You should also consider your friend’s husband. Even if your friend is fine with the two of you dating, it’s possible her husband may feel uncomfortable about having his wife’s ex around.

Also, why  didn’t it work out between your friend and this guy? Did he have a temper? Was he controlling? Or maybe, they just weren’t compatible. Either way, these are all things to consider.

If your friend is cool with you pursuing her ex, my main advice to you is to still be mindful of the fact that they used to date. Take things slow. For example, a sloppy make out session at your friends New Year’s party isn’t the best way to warm her up to the relationship. Let your friend ease into the idea of her ex and her friend together.

With all that being said, list out the pros and cons about dating and fill me in on your decision. I love a good relationship dilemma. Good luck on your quest for love!


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