Dating a Friend’s Ex

Twitter: @1PeopleMW

A week ago a dear friend, who happens to be an ex-girlfriend, asked, “could a friend ever date any of your ex-girlfriends?” I’d imagine dated an ex’s friend could also apply here, minus the desire to maintain a friendship. Now before I go any further, I feel compelled to inform you, the reader, I am neither the friend nor the ex in her scenario; meaning she’s not checking to see if she could date any of my friends or me dating any of her friends. Also, the reason she asked me directly is because of my work with the G-Spot column (in AIM Magazine). Apparently an ex-boyfriend of her middle school friend approached her recently, some 30 years after the fact (which I do not say in a judgmental or condescending way), and she thinks there’s no scenario in which the two of them could get together.

I answered, “Yes; I do believe there is a scenario in which a friend could date an ex of mine wherein he and I remain friends.” Then I immediately followed up with, “if the ‘EVER’ in your question were in very large font and all caps, then my ‘yes’ would be in very small font, lower case.” Yes, I did actually say that. (I’m a very visual person; even I when speaking.) I further explained the scenario must be satisfactory in five categories: Time, Tenure, Tact, Track record, and Truth; with this list building in order of importance from least to greatest.

Time—as in how much time has passed. The minimum time before my friend could begin a courtship with an ex of mind is the length of the relationship, in months, divided by the sum of 1 plus the number of breakups during the relationship; or R ÷ (1+B). Yeah I know, you’re probably thinking, “Okay, whoa! Who does this guy think he is coming up with a formula for how long someone should wait to approach a friend’s ex, especially when there are those who feel it is never good to do so ever?” Maybe I am a little crazy for “going there,” but hear me out first. Since we’re already “here,” let’s just have a little fun with this topic.

For instance, if you were in a relationship for 5 long years and broke up only once during the relationship, which constitutes a serious relationship by any standard, then according to my formula your friend should wait a minimum of 30 months (or 2.5 years) before approaching your ex to begin a courtship, keeping in mind we are talking about ex girlfriends not an ex wife. By the same token if you’ve dated someone for 3 months and broke up like 5 times, which I deduce is not a very serious love affair, then the friend should only have to wait a minimum of 15 days before making a move without fear of retaliation. After, the point of this is maintaining the friendship. If not, then none of this matters

At first glance the formula’s integrity seems to break down when you take into consideration a 10 year relationship in which the couple broke up twice every month; because “breaking up to make up” was just “their thing.” But this is precisely why time is not the only factor. In fact it is the least significant of the 5 categories. If any of the other four are not satisfied then no amount of time would be sufficient for a friend to date my ex.

Tenure—as in how long you have been friends relative to beginning the relationship with the ex. Although tenure is fourth in order of importance (i.e. level of importance is in reverse order of presentation) it just might be the factor that weights the heaviest in my decision to continue with the friendship. If we have been friend for a long time, especially good friends, then I would be less incline to walk away from the friendship.

Tenure also plays a role in how sound his decision to pursue my ex appears to others in our friend circle. If we have been friends for a long time, trusted friends, then he must really like the ex to risk our friendship. Reversely, a friend of short tenure, especially if meeting him after forming a relationship with my now ex-girlfriend, would leave me guessing; wondering if he’d always had eyes for my girl. So in a word tenure is about his credibility as a friend to have legitimately stumbled into this situation.

Tact—as in how my friend and my ex go about the courtship until it becomes a relationship, and the manner in which they reveal the relationship to me and the others in our friend circle. Discretion (not deception) and timing are paramount in such a delicate situation. Tact is important because it, second only to his track record, most directly speaks to his character, and, more than the other four factors, will survive longest in my memory; as Dr. Maya Angelou wisely stated, “I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.”

Tact is about how well I feel about the way the friend handled the entire situation. And when we are old and gray, or I should say grayer, I will most remember how his handling of the situation left me feeling dignified. In word tact is about respectability.

Track record—as in the friend cannot have a track record of dating his friend’s exs (assuming your ex hasn’t dating any of your friends previously as well). Even if this is the first time he’s done it to me, if he is notorious for chasing “sloppy seconds” then all bets are off. Enough said!

Ol’ snake in the grass! Oh, sorry… ‘nough said.

Truth (or Truth-in-love) —as in, how real is the friend’s connection with the ex. As the older folks would say; this one is for all the marbles! Truth-in-love is the most important factor, hands down. If this relationship is to be, even at the risk of losing a friend, then it must be real.

Under no circumstances could their courtship or relationship be about me. Neither of them can be pursuing the other as a way to spite me; which by the way has happened to me in the past. The intent must be about their sincere attempt to find “the one.” (As stated in the October 2012 edition of AIM Magazine, I don’t subscribe to the concept of a soul mate, i.e. 1 in 7 billion, however I do believe the amount of people in the world that are a person’s best match is still less than one thousandth of a third of a percent, e.g. more like 2 million out of 7 billion; thus is still a very select few.)

Even if the union passes the time, tenure, tact, and track record tests the absence of truth-in-love is the ultimate deal-breaker. Truth-in-love should govern the other four requirements. It sees to it that the time that passes helps to defuse suspicion of the two checking out one another during my relationship. Truth-in-love, as well as his track record, reinforces the tenure of our friendship, lending even more credibility to his pursuit of the ex. And the tactful way in which the two courted then confirmed their genuine attraction towards one another shows that it was a well thought out endeavor.

Now you know my take on the topic. But as always I invite you to make up your own mind, and then share that perspective with others. For me, it would be hypocritical for a philosopher as myself to stand in the way of true love when everything has been done in order. Yet I will admit, even though I have articulated a scenario in which it would be ok to date a friend’s ex, I can appreciate that it is still taboo. Trend softly.

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