How to Date an Ex’s Friend

We don’t stop appreciating a Picasso if we own a great Monét, and we don’t stop noticing other women just because we are in a great relationship. Nature, art, poetry and femininity have boundless magnificence we can always enjoy as civilized human males. But what if one of those joys that is attracting your attention in a new and exciting kind of way happens to be the best friend of the woman you recently broke up with?

There’s only one thing more uncomfortable than dating the best friend of your ex, and that is dating the ex of your best friend. You probably wouldn’t be thrilled if the best buddy that you meet for happy hour three nights a week was warming up his lonely nights in the arms of the woman that you were in love with just last month. It would be very awkward for you to date his former lover, too.

Of course, that is exactly the situation you would be putting your new girlfriend into with her best friend (your ex). It’s not quite as tangled as how you can really be your own grandpa, but it does have the potential for bad blood, broken friendships and hard feelings. Before you wander into irreversible turmoil, take some time to make sure this is the right move for all parties.

It is normal to have small unrequited flirtations with a friend of a girlfriend, just as she certainly sees some men that she might otherwise be attracted to in your group of friends. Your bond, commitment and the fulfillment you find in your relationship keeps these potential feelings in check.

But you do need to honestly ask yourself, “Am I interested in my ex’s friend for the right reasons, or is it just pent-up sexual tension from the months that she was the forbidden fruit?” Be honest when you weigh your attraction, feelings and the potential for a future together before you move forward.

A person’s friends are the dearest possessions they have, and a tight-knit group can get each other through all of the hurdles and hard times that life throws at you. True heartfelt passion and love can be justifiable cause for dating your ex’s friend. But it is definitely not cool to use her group of friends as a harem to satisfy your lusty urges. That’s a big no-no.

“The fact is that you no longer have a commitment to

your ex. It is right that you should both move on.

Just make sure enough time has passed.”

Was it the kind of breakup that you both saw coming for a long time but held on for a while for convenience? Or was it a sudden and emotional upheaval that one or both of you did not expect? In the first case, things may have ended gradually in stages until there was just nothing left. Perhaps it was an amicable parting, and you both went your separate ways.

But if your relationship was torn apart by betrayal or some other disruptive occurrence, you both may just need time to heal before you both realize that you can’t live without each other. If torn emotions with jagged edges are still flying around untamed, it may be the wrong time to pour salt in the open wound.

Amicable or not, many long-term relationships suffer breakups that are only temporary. Make sure you don’t undermine your real lifetime partnership for something that is likely to be temporary if the fat lady has not yet sung the end to your relationship with your ex.

Some breakups require that all contact be severed forever. Sometimes your ex may have dumped you over a principle you violated — fidelity, forgetting every special occasion, choosing the guys over her once too often. Whatever it was, she may consider it to be a betrayal by any of her friends who would take your side or who still find any redeeming social value in your existence.

Even if the matter seems petty to her friends, it is a big deal to your ex. Dating her best friend could mean they both lose the best friend they have in the world for all time. That is asking a lot of a new girlfriend and a severe blow to the woman you once loved. Think long and hard before you put a girl you care about in a position that could damage part of the foundation of her life.

If civilized communication is possible, try to talk to your ex about dating her friend before you jump in with both feet. She may be totally supportive of the idea. She may be a little shocked, so you will have to assure her that these feelings are new for both of you and there were no such thoughts when you were together. In any case, she is likely to feel better about it if she hears the news from you instead of finding out on Facebook or from a friend.

The fact is that you no longer have a commitment to your ex. It is right that you should both move on. Just make sure enough time has passed so you are certain about the finality of the past relationship. Take some time to consider how you would feel if she started dating your best friend and act accordingly. Make sure there is potential love in your heart for the best friend of your ex-girlfriend.