Love & Sex

True Stories: Dating My Ex’s Friend

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Should I have expected trouble?

Bob's erection took on the consistency of Silly Putty. He repositioned himself on my sheets, looked down, then up at me. "I think the condom has come off," he noted clinically, as if I were a lab monkey and he were Jonas Salk. Under different circumstances, my vagina might have played a role in curing polio. Right now, it was semi-occupied by a blue-eyed, thirty-year-old Seattle engineer who held two patents, but little sway over his penile carriage. He was six years older than me, and I'd foolishly imagined that that would make him a sophisticated lover. 

"You think or you know?" I asked, alarmed by the condom's ambiguous whereabouts. 

Bob withdrew entirely. "It has definitely come off," he answered, realizing he was unsheathed. "It must be still inside you. Do you want to get it out? Or do you want me to try?"

So far, nothing about this Saturday night had gone according to plan. My heart recently broken, I'd seduced Bob in an attempt to mend it. As such, I'd called and told him I'd made spaghetti sauce from scratch and was about to watch an episode of Northern Exposure on VHS. Not the most scintillating offer, to be sure, but I was newly unpaired and late to such machinations. It was lucky that I was in superb shape and owned many black underthings. 

"Should we give it another go?" Bob asked, as I noticed we'd gotten spaghetti on my bedspread. 

"You're down there anyway," I said. "See if you can reach it."

"I should use my hands, right?" 

"Well, I have pliers in the junk drawer." 

"No, that won't work," he replied, missing my joke. 

"Oh, Jesus. I'll get it myself," I said. And after much contorting and nearly giving myself an appendectomy, I located the rogue latex barrier. In the background, Rob Morrow and John Corbett exchanged laconic quips about their beloved Alaskan hamlet.

"Should we give it another go?" Bob asked, as I noticed we'd gotten spaghetti on my bedspread. 


While this remains my worst sexual experience (and possibly Bob's), Bob was a decent, smart guy. We shared a bunch of the same friends and were amiable when we ran into each other at parties. So when he asked me to peruse used bookstores and then grab coffee one afternoon almost a year later, I accepted. To me, it was clear this was a platonic outing, and we had a surprisingly good time. We happened to be reading different translations of Camus' The Stranger, and we compared observations over mochas at a battered coffeehouse that pre-dated our city's association with caffeine. I'd always had as many guy friends as girlfriends, and Bob and I fell into an easy routine of hanging out every few weeks. We related to each other's inner nerd, and I assumed we'd maintain this easygoing, occasional palling around.

In friendships, as in relationships, it's universally recognized that opposites attract, but it's equally axiomatic that like attracts like. So it was maybe unsurprising that Bob's housemate Keith and I found ourselves flirting whenever we intersected. I'd known Keith since college, and he was the one who'd introduced me to Bob in the first place. Keith and Bob had much in common: both were well-educated, thoughtful, in good shape, and could hold forth on a myriad of topics. Keith, however, was the more playful of the two. And, unlike in college, we were now both single at the same time.

Now, I'm aware of my flaws — perfectionism, a tendency to overanalyze, a Greek temper that occasionally gets me into trouble — but I've never cheated on anyone, and I'm open with the people I date. I don't view dating or love as power plays or sources of validation. So you'd think I'd have known better than to go out with the close friend of someone I'd already slept with.

When Keith took me aside at a Halloween party and we began making out… it didn't occur to me that trouble might arise.

But even though I was now twenty-five, I hadn't caught on that I seemed to be perceived as attractive — as someone for whom certain guys might compete. I still viewed myself as the frizzy-haired and studious teenage art-geek I'd been, the girl who had to ask her then-boyfriend to the prom because said boyfriend, also an art-geek, had been "philosophically opposed to proms." In my high-school graduating class, I'd won Most Likely to Become President and Most Liberal by landslides, but didn't receive a single vote for Best Eyes or Best Legs. I know, because I was editor of the school newspaper and tallied the results. As a feminist, I officially didn't care; as an eighteen year-old, I was crushed. 

So Bob and I continued swapping Kurt Vonnegut paperbacks and seeing subtitled films, and when Keith took me aside at a Halloween party and we began making out in the kitchen and slept together that night, it didn't occur to me that trouble might arise. Bob had been out of town that evening, but after Keith and I went out a few more times, I assumed Keith had told Bob — his housemate, after all — about our dates. (Another thing I hadn't yet learned: straight guys aren't always so quick to share emotionally-loaded information.)

It was over bowls of tomato-basil soup at a low-key, now defunct restaurant that I inadvertently told Bob myself. As the weeknight rain poured outside, Bob mentioned a film he thought we should see. I heartily recommended Bob's pick, and said Keith and I had really liked it and that he probably would, too. I was off-handed in my remarks and more focused on the soup, my favorite. 

"What do you mean you and Keith liked it?" Bob asked. 

"That we thought it was good. As in, 'not un-good.'"

"Yeah, I got that. What did you mean about you and Keith?" Bob looked at me quizzically, his eyes tinged with hurt. I began to realize he didn't know that Keith and I had been out a few times now.

I proceeded kindly. Bob and I were friends, and we had always treated each other with respect. The last thing I wanted to do was cause him any pain. Then I started wondering, "Why is Bob hurt?" Surely he hadn't attached any emotional content to our singular, disastrous sexual encounter over a year ago. Or had he? 

Surely he hadn't attached any emotional content to our singular, disastrous sexual encounter over a year ago. Or had he?

I discovered the answer, as Bob, the straight-laced engineer of Scandinavian descent, stood up in the middle of the assembled diners and yelled, "Litsa, you're just into cold-hearted fucking!"

Everyone turned to look. "Sit down," I hissed and glared at him. Not only am I one-hundred-percent Greek, but I'm Spartan at that — I'd dealt with emotional outbursts my entire life and gave as good as I got. Bob returned to his chair, but it was clear he was seething. In moments, our relaxed meal had turned into an Edward Albee play. 

"You know, I've been yelled at by my mom and my aunt, who might just be the world's best yellers. So don't think your pathetic Norwegian attempt is going to rattle me." Admittedly, this might not have been the point, but I was mad now, too. No man had talked to me this way and they sure as hell weren't going to start now. More importantly, from my standpoint, I hadn't done anything wrong.

"Listen, I'm sorry if you're hurt," I said. "But are you seriously upset I've gone out with Keith? You and I slept together once and it was a train wreck." Bob flinched. (Still another lesson learned: don't tell a man your sex with him was a "train wreck," even when that constitutes an understatement.) I sighed. "Bob, you know I would never deliberately hurt you. But you and Keith are housemates, for God's sake. I assumed you knew."

"That's just it," he said, more quietly now. "Keith and I are housemates. Couldn't you have gone out with someone else? Did it have to be Keith?"

Oh, okay. Now we were getting somewhere. 

When Bob dropped me off that night, we hugged tentatively and said we'd get together soon. It was a testament to our youth that I think we both meant it but, of course, we never saw each other alone again. Weeks later, he called and asked me to mail him the only copy of a short story he'd written. I didn't do it. Half-hearted reconciliation or not, no one yells at me in public and gets their shit back. 


Keith and I soon fizzled out amicably, realizing we had little in common. But it was Bob I ended up missing. We all enter into romance knowing things might get complex. What Keith and I experienced, though, never surpassed mere pleasantness, so the parting was easy. (We, too, remained friendly when we saw each other.) Because Bob and I had been fully clothed during almost all our time together, we talked more. We learned of each other's families and career aspirations and philosophical beliefs, because in addition to movies and authors and mochas, that was our only way to connect. And our burgeoning friendship had ended with hurt feelings on both sides, because I'd slept with his housemate. Strangely, Bob never got mad at Keith; in his mind, I was the only transgressor.

We've all had the quasi-pal who threw themselves at our partner, thereby betraying our trust. But most of us aren't assholes and don't want to hurt anyone.

Some friends hold that each other's exes are off-limits, but I can name scads of friends who dated other friends' exes, often with outstanding results. Again, like attracts like, and there's a good chance each of us has a friend who is similar to us, but a better fit for someone we once dated. I know two such couples, in fact, who have been happily married for years. Should they have forgone such fulfillment merely because a compatriot sniffed the bits first? Sting met Trudie Styler, his longtime wife, because she was friends with his first wife. What would our khaki-wearing cohorts listen to today had he not found such bliss? Is it more important to be loyal to your friends or your own potential for love?

As is often the case with love and sex and fair-minded, consenting adults, the answer seems to be, "It depends." None of us wants to be on guard when introducing our partner to our friends. We've all had the quasi-pal who threw themselves at our partner, thereby betraying our trust. But most of us aren't assholes and don't want to hurt anyone. Both romantic and platonic feelings, can run profoundly deep, of course, stirring parts of us we didn't know existed, with unpredictable results. The resulting energy can warm a home or burn it down. 


Long ago, I learned far better tricks than pasta sauce and dramedy. As for the larger question: would I go out with Keith again today? Yes, probably. I had no reasonable expectation Bob would care or be hurt. And what if Keith had turned out to be more than a fond anecdote? If we let it, wisdom comes with age. I would discuss things with both men and take it from there.

An unwavering verity I've learned, however, is to keep the black underthings handy. Love and friendship will always be complex, but a few rare elements remain joyfully simple.

Litsa Dremousis is a Seattle-based freelance writer. Her work has appeared in The Believer, Esquire, McSweeney's, the Seattle Weekly and on NPR. She’s currently finishing her first novel. Do yourself a favor and follow her on Twitter.