The Moral Conundrum: Is It Ever Okay To Date Your Friend's Ex?

by Kenzie Aryn

Post-college dating, especially in a city like New York, is challenging and frequently ego-depleting. Thanks to online dating websites and applications like Tinder and Hinge, it’s feasible to have seven (or more) dates per week.

Not only is it exhausting, repetitive and sometimes taxing, it can be frustrating. The more you date the more you begin to question whether you will ever find “the one.” That brings us to the question at hand: Is it acceptable to date the ex of a friend? Before viscerally responding “no” to breaking the guy/girl code, hear me out.

Let’s set the stage: Your friend was dating an amazing girl. During their relationship you found yourself developing feelings that went far beyond a physical attraction. You two just “clicked.” Fast-forward: Their relationship ended, she’s single, now what? Do you pursue her or do you decide it’s not worth the risk of losing your friend?

Some would argue that this decision comes down to whether you choose to listen to the devil on your right or the angel on your left. Others would say, “Absolutely not; the exes of friends are always off limits.” Still, others maintain that an ex is an ex, and once they’ve moved on, the subsequent choices he or she makes are no longer the interest of the former partner.

I prefer to redistribute some relationship responsibility to fate, and what is meant to be will be. I believe if two people are meant to end up together, they will ultimately find their way to or back to each other. However, as a relationship researcher, I recognize and sympathize that fate is not always in our favor. But let’s consider the statement: The heart knows what the heart wants. I ask the question again, can the code be broken?


Real friends vs. “Facebook” friends

As we mature, friendships become more selective. In reality you are not “friends” with your thousands of Facebook friends. If this friend (who dated the person you want to pursue) is a “Facebook friend,” you can stop reading right now. There will be no love lost and I wish you luck in your pursuit. However, if this is a true friend, take a minute to consider the risk of losing him or her forever. Ask yourself if this friendship is strong enough to handle the repercussions? Losing a friend over a relationship, which may or may not work out, is indeed a gamble. Are you prepared for the potential consequences? If so, move ahead with caution.

Previous relationship duration

Was the previous relationship one that ended at the altar or was it a fling? The shorter the relationship, the easier time you’ll have convincing yourself (and everyone else) to move forward in your pursuit. No harm no foul.

Post breakup timeline

When did the split occur? A month, six months, a year, six years? Does it matter? Is there a point when an ex is no longer referred to as “the ex” and therefore deemed acceptable for anyone to date? As a general rule, I would say the longer you wait, the better. I also believe, however, that life throws us curve balls. Love has a funny way of coming at a time when you’re not looking and least expecting it.

Reason for termination

A relationship with the ex of a friend is undoubtedly easier to justify if said friend ended the relationship. We often have a tendency to romanticize experiences. Ask yourself, did their relationship end because of the ex, and if so would he or she be any different in a relationship with you?


With an increased awareness of engagement and marriage announcements, because of social media, you cannot help but feel some pressure to find “the one.” Do not allow your notification globe to pressure you into taking a risk (because of your age) when you’re not fully committed. Age can be a double-edged sword in this situation.

Why this ex?

We all know the old adage, “we want what we can’t have.” It is important to take the time to consider whether a relationship with this person has actual potential. In most cases, a one-night stand is not worth the long-term drama. Again ask yourself, why this ex? What makes this person so special? Is the pursuit of this relationship worth all the drama and negative consequences that could possibly ensue? Is there really something about this individual that you cannot imagine finding in anyone else?

If you decide yes, the code can be broken…

Make sure you both agree what this relationship is, what it could be become and what you both want. If you are in agreement, it’s time to break the news to the friend  (your overlapping social network will also be grateful once this step is complete). It is far worse for the friend to learn about the relationship via another party or from social media. Discreteness can easily resemble secretiveness. It is important to be upfront with your friend, but be forewarned: Even though romantic feelings may no longer exist, your friend may still feel betrayed. I would expect the worst and hope for the best. I never said it would be easy, but it may be worth it in the long run.

In many ways, dating the ex of a friend is a “damned if you do damned if you don’t” situation. I know of many examples of people who have been in this exact situation. The results have varied from marriage to bonding over a mutual ex. Still, others have taken the risk and over time, the relationship did not work out, leaving them with both an ex-friend and an ex-partner.

You may or may not be asking yourself, what would I do? Consider the questions I posed above. Personally, I will always push for the possibility of true love and hope that fate intervenes. However, it comes down, ultimately, to who is more important to you long-term -- the friend or the potential partner? The risk may be worth the reward, but make certain you are prepared for the potential loss(es). Did I mention that dating the ex of a friend is not a simple yes or no?

Photo credit: CW/Gossip Girl