Playing with Matches

by Jennifer Garstang August 5, 2013


By Jennifer Garstang

Unless you have a Yenta on your side… or you’re one of those disgustingly cute people who met your disgustingly cute soul mate at the age of four and have been part of a disgustingly cute couple ever since, you probably have an ex or two. This means you’ll have to answer a common question in the world of singledom: “Should I try to stay friends with my ex?”

To begin answering this question, let’s examine case studies of individuals who held polar opposite opinions on the subject (Ooh, aren’t we methodical and scientific!)


Opinion #1: Always stay friends with your ex, and don’t waste any time about it. In fact, you should introduce her to your current girlfriend right away because they will certainly be the best of friends!

My first serious boyfriend believed that people should always stay friends with their exes. A romance, he reasoned, is first and foremost a friendship. After investing months or years building that relationship, the thought of throwing it all away simply because you don’t work romantically seemed ridiculous to him.

And so, a week after we became an official couple, when his cell phone began to play “Tiny Dancer” in typical ring-tone fashion, the following ensued:

“Hello?” he said. “Hey you!… sure! That sound’s great! H­ang on a second…” Covering the mouthpiece, he turned to me and whispered, “hey, wanna come to dinner with me and my ex?”

That one sentence deftly obliterated my warm, fuzzy, new-relationship bliss, unleashing in its place a terrifying vortex of jealous-girlfriend insecurities that I’d never-before known lurked within me: Who is this man-stealing Shiksa trying to keep her claws in my guy?! That manipulative %^$! If I say ‘no,’ I’ll just be the “jealous girlfriend,” and have to tell my boyfriend I don’t trust him… maybe I don’t trust him…

My thoughts swirled and congealed into the words: “Um… sure?”

“Great!” he removed his hand from the mouthpiece. “See you tonight!” Then flipped the phone shut.

We didn’t go to dinner with his ex, but his insistence on maintaining contact with her led to some turbulence throughout our relationship. However, after our own breakup, his tenacity in maintaining contact with me (along with his shocking ability to weather the storm of my wrath) is a big part of why we now have a warm and caring friendship.


Opinion #2: Never Stay Friends with your Ex. Ever. In fact, you should find every possible reason to hate them, and take pleasure in the shortcomings of their new partner.

My best friend throughout the last two years of college believed that it was a bad idea to EVER stay friends with an ex. He felt, in fact, that it was healthy to reflect on their bad qualities after a breakup. That way, you would have no complicated attachments when beginning a new relationship.

And so, after I broke up with my first serious boyfriend, we spent lots of time talking about our awful exes, expounding upon all of their flaws, marveling that we ever thought dating them was a good idea, and laughing our way through the breakup pain.

Then we started having feelings for each other.

It seemed promising – we found each other attractive, and got along great. The problem was, the stakes were too high.

Turns out, it didn’t work, and our efforts resulted in a big, messy, pseudo-relationship jumble, which ended up damaging our friendship anyway.


Opinion #3 (aka the right opinion (aka MY opinion)): Take it on a case-by-case basis; just make sure your past relationships don’t inhibit your future ones.

After collecting a few exes of my own, I came to a conclusion for myself: there is no catch-all “always” or “never” answer. If you want to stay friends with your ex, it’s important to first ask: “Will the relationship I maintain with my ex get in the way of new relationships?”

If the answer is yes, then you’d better stop and really think about what you’re doing. That said, if your ex is someone you enjoy being around, and you can find a way to do so while being sensitive to your new romantic interest, then a blanket philosophy is no reason to throw away a valuable friendship.


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