3 – 2 – 1 – Action!

Close-up on me, outside of my now ex-boyfriend’s apartment, arms around his neck, promising that we’d still be friends.

Cut to:

Me again, three years later, watery-eyed outside of work, texting my next ex-boyfriend, telling him that of course we could make a friendship work.

Cut to:

Me still, driving to meet my third ex-boyfriend to give him back his spare keys, determined to regain our friendship.

And: credits.

Three guys, seven years total, and nothing overlapping amongst them – except the insistence that I could transform three broken-hearted ex-boyfriends into three bosom buddies with nothing more than devout stubbornness. Because honestly, breaking up can be dealt with, but completely losing someone you once loved, allowing them to mosey out of your life without so much as a parting gift, that’s truly heartbreaking.

Never did I mind that I broke up with all three of them, because I offered them the gift of my friendship, which is, of course, invaluable. So I wasn’t terribly shocked when all three took up my offer – my ridiculously stupid offer.

And this is how it turned out – all one, two, three of them.

1) First Love Syndrome

This one was my lost-my-virginity, picked-out-our-future-kids’-names guy, so that’s saying something. We both cried during the break-up, and I forced my friendship on him like a drunk, single girl hard pressed for a New Years midnight kiss. As such, it went about as expected: he developed a drinking problem, and I developed a great talent for convincing him to not fall asleep on the lawn outside the St. Patrick’s Day party. This friendship lasted three years – various awkward patches cropping up in the midst of relative normalcy.

There was the time he decided to pursue my best friend and roommate in spite of my protests at potentially having to listen to them have sex. When word got back to me that the first and only time they tried to get busy, he got relationship-ending whiskey dick, I thanked God for smiting a girl who chose dicks over chicks, and a guy who told me I was his closest friend – until that got in the way of getting off.

Then there was the time we split a pitcher of Magic Hat the night before spring break, and he tried to seduce me into leaving my boyfriend with romanticized memories of our past. I drank steadily for two weeks, and debated the merits of rekindling former romance in lieu of pushing forward with the guy I lived with and loved, ultimately sobering up and realizing how stupid it is to dwell on the past. Meanwhile, adding insult to injury, he hooked up with some hairdresser back home. That’s what friends are for, you see: messing with their love lives in pursuit of getting laid, then folding last minute when an easier mark comes along. Needless to say, I didn’t see the need to speak to him for some time after that.

Eventually, though, we mended the bridge he’d burned, and an actual friendship formed. He sent me texts of his misadventures in dating, I gave him advice, and every so often, we’d have lunch at a diner and catch-up about life in general. Things seemed to be good.

Until we went out dancing with friends on one of his post-grad visits back to town. I was the Goose to his Maverick, pointing out potential marks to pursue – until he grabbed me, sloppy-kissed me, and informed me he was coming home with me that night. Sorry pal, I never got that memo.

Now he lives in LA, frequents 18+ foam parties, and is developing his father’s bald spot. Or at least that’s what I hear – I defriended him around the same time I “forgot” to give him my new cell number, and I think that’s for the best. Any friend who continually dumps drama all over your life is ultimately disposable, First Love Syndrome, or no.

2) Sloppy Seconds

Number two was the unattractive guy I should have used as a transitional object and then trashed – he’s actually the reason my therapist’s kids will get to go to Ivy League universities. But, like a heroin addict transitioning to methadone, I clung to my stupid addiction to the point of trying to turn an emotionally abusive relationship into an emotionally abusive friendship.

There were some weeks to go before I could move out of our shared apartment and into my new “70s porn apartment,” complete with shag carpet and spotlights over my bed, so it was either friendship or seemingly infinite awkwardness. We compromised on watching Mad Men. Silently. From opposite ends of the couch. So much for avoiding infinite awkwardness.

For those of you who have not seen Mad Men, there are some sexual undertones, and occasional overtones, setting the mood for a foray beyond friends into benefits. Over the next year, these benefits included not only sex, but a lot of ugly crying, both in front of him and on my own; dealing with his fluctuating need for my body and his need for space, which was unpredictable to say the least; and convincing myself that sex with an ex is convenient and impersonal.

It drove me crazy.

I heard he was on a date and called him incessantly until I reached him, then begged him to take me back. I stalked his neighborhood, trying to find the new apartment he would never take me to because he didn’t want his roommates to know about me – the best part of that one was passing him at an intersection, locking eyes, and pleading with the universe to let a curbside tree topple onto my idiotic head. I ended up at his house at three in the morning, throwing a Vitamin Water bottle at his window because he had shut me out again, and I was determined to change his mind.

Basically, the situation was incredibly healthy for me.

I was addicted to and manipulated by someone who knew me well enough to reel me in when he wanted, and how to hurt me the most when he didn’t. But we sure were friends, at least when our shared social-group got together, and I clung to that word for my entire 23rd year until my self-respect finally stopped cowering in a corner, and bitch slapped me across the face.

He’s long been cut out of my life, blocked on every level of social media ever since I ended things for good. I hear he lives in New York now, and have a suspicion that he’s likely not dating anyone (for every NYC woman’s sake, I hope not), and will most certainly dedicate his entire life to work and wealth. And who wants to be friends with someone like that?

3) Last, But Not Least

Shortly after my disastrous attempt at sex with an ex, I sensibly decided to start sleeping with my internship supervisor. Or rather, he kissed me in the parking lot of a bar after beating me at a game of pool, and, within a week, we were sleeping together.

Before you cry ‘sexual harassment,’ I had texted him “Hey” circa 1AM the previous weekend, and we all know what that means.

Within a month, we had said, “I love you.” Within three, we were convinced that we’d get married, and within six, I cheated on him with Guy #2.


Because Number 3 loved me immensely, accepted me fully, and we were connected on an unparalleled level – I was the happiest I had ever been in my life. So I set out to ruin it, and I did. Our torrid affair began in February, our love story ended in July, and our attempt at friendship came alive in August, with a vengeance.

I called him daily, and for hours on end, talking and laughing as if nothing had changed. I had phone sex with him on the night of my birthday, after Guy #2 bailed with the excuse that we had spent too many hours in a row together. And I kissed him when we met to exchange spare keys.

By September, I had moved in with him, and by October we were engaged. Two years later, and two weeks ago, we got married in Las Vegas, came home to our loft apartment, and started our lives as a married couple. I should have known we could never be friends.

Maybe there are people out there who can successfully befriend their exes, after the heartbreak is over, and the healing too. I’ll raise a glass to them as soon as they present themselves, because I’m not entirely sure it’s possible. After all, my attempts to befriend my exes have resulted in drama, misery, and marriage, and I firmly believe in the Three Strikes policy. So I guess I’m out – of exes, their friendship, and the belief that the two can ever coexist peacefully.


Liz Furl is hanging out in a loft in Rochester, NY doing one of the following: 1) Working on her podcast; 2) Writing for FTS and/or other websites clamoring for her talent; 3) Watching her cats be general idiot nuisances; 4) Plotting to leave the soul-crushing grasp of Cubicle Land; 5) Devising ways to take the world by storm; 6) Slowly detoxing from iPhone games and Netflix; 6) Drinking some cheap wine or expensive beer, possibly combined with any of the above. You can find her at LadyBitsPodcast.com, @LizFurl on Twitter, and even on Facebook, if you ask nicely.


  1. omg I’ve lived through one and two types of guys spot on! Maybe I’ll have your luck and find the one the third time around 😉

  2. TotallyNotASarahYouKnow Reply

    Present! Well, although I’m still friends with my ex, he IS a manchild who heavily invests his free time in video games and avoids affection like The Plague. Probably explains the lack of drama.

    • That’s a good ex to have — low maintenance. I probably should have thought of this before I dated 1 & 2. . .

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