True Stories: Dating My Ex's Friend

Should I have expected trouble?

By Litsa Dremousis

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.)

Commentarium (32 Comments)

Aug 29 11 - 12:46am

I really loved this. Really well written, and funny. I do disagree on one point, though: There are no better tricks than pasta sauce and dramedy.

Aug 29 11 - 9:35am

Thank you, Internet stranger. What a great comment to read 6:15 a.m. here on the West Coast. Cheers.

Aug 29 11 - 8:31am

Great piece - really well-written - but speaking as a fiction writer, not returning his story was the mark of a cold-hearted bitch.

My last ex and I broke up on truly terrible terms, and I never returned a flannel shirt of hers. She never returned quite a lot of my sex toy collection, which I didn't mind, a fairly valuable painting, which I *mostly* didn't mind because it wasn't a good stage in my life for material goods and because the painting reminded me of her - and the only complete copy of my latest novel.

Unlike the rest of my things that she kept, that file had no material worth but quite a lot of emotional worth - it was a labor of love and a metaphorical chronicle of the breakup, which she may have realized after she read it. I begged her to send the file, because I stupidly had not backed it up online, and my home had been burglarized and my computer stolen. She refused.

Dating his roommate could happen to anyone. Not realizing he still had feelings for you could also happen to anyone, although happens easier to the people who like to pretend to ignore it. Getting angry that he shouted is justifiable. Not giving him back his story makes you a complete tool. You lost all my sympathy and I barely skimmed the rest of the story.

Aug 29 11 - 11:32am

agreed. HEARTILY.

Aug 29 11 - 3:07pm

Yeah I'm gonna second this. If you still have that copy, Litsa, you should send it to him. It's wrong for you to keep it.

Aug 29 11 - 3:34pm

In case "Northern Exposure" on VHS and every other discernible detail didn't underscore this point, I will explicate: this story occurred 19 years ago. I included the un-returned short story in order to be fair, i.e. to point out I'm not the hero and he's not the villain. That this occurred in shades of gray, as life usually does. Notably, no one of either gender takes umbrage w/ the fact Bob screamed at me in public in an attempt to humiliate me.

Aug 29 11 - 3:43pm
one two

His mistake of yelling was purely emotional. Your mistake of keeping his file is premeditated assholeness.

Aug 29 11 - 4:12pm

Once again, I'm gonna agree with a previous responder. I've enjoyed your other stories Litsa, and obviously this happened too long ago for it to mean anything. But was a couple seconds of public humiliation (in front of strangers that don't matter) really worth basically destroying the only copy of someone's artwork? Him yelling at you wasn't the right thing to do, but every once in awhile our emotions get the best of us. I also think you misunderstand why public outburst like that happen. Do you really believe he yelled at you with the explicit intent to humiliate? I seriously doubt it. More likely he was flabbergasted that someone so close to him could have disregarded his feelings when it came to their decisions on who to have sex with. Not saying you didn't have a right to sleep with Keith or that you did it on purpose, far from it. I'm just saying there's little to no chance he yelled like that to embarrass you. Even if he had, it shouldn't have mattered that much to you at all.

Thanks for including the detail anyway - it performed the function you wanted it to, at least. It's great seeing how this connected with your Halloween story, and you're a gifted writer.

Aug 29 11 - 4:19pm

Ryan, I appreciate your adult and nuanced response. We agree on a number of points and I like your approach to the ones on which we differ. All the best.

Aug 29 11 - 4:39pm
Charlie Smith

It is an interesting detail, Litsa, and full of meaning. For example, it may well have been a mediocre time-based essay; but by now I'm sure he has inflated it to being considerably better than the Gettysburg Address. Of course, this again confirms my belief that any sexual encounter that contains the sound, "Ooooopps!" foretells a rocky relationship.

Aug 29 11 - 8:00pm

I'm confused. You're angry at him for divulging your sexual habits in public, or at least how he felt about them. Yet you in turn divulge his sexual shortcomings with you in public, and keep his story? Sounds like the only mistake he made was not publishing "Litsa, you're just into cold-hearted fucking!".

I doubt he wants this published anymore than you wanted him to yell.

Aug 29 11 - 11:13am

Fell off? I once had a condom break during some really awesome sex (damn you trojan). Man, that was a tremendous mood killer. It was a one night stand and round two for us that evening. But I can totally relate that kind of thing really makes it completely unsexy in every imaginable way and no matter how good it was up until that point, everything suddenly sucks.

Aug 29 11 - 12:19pm
Jane Anderson

First- liked this! Lost condom? Been there, done that. Yelled at in public 'cause he was upset and I had no clue? Been there, done that. Dated the room mate of a friend? Yep, and married him (the room mate.) And lost a whole lot of letters and stories that I'd written, during the marriage, during the divorce. In defense of the author, she was young. And, writers need to learn to back up their material-- even if it requires a trip to a copy shop.

Aug 29 11 - 12:53pm

I liked the rest, but your opening was awkwardly written and stretched...

and Salk didn't cure polio. His vaccine can prevent polio.

Aug 29 11 - 4:11pm
Charlie Smith

Drat! It's a wonderfully funny story, but certainly not Dad-readable!

(For the record, my work used to involve working with Litsa's Dad.)

Aug 29 11 - 6:18pm

Is someone you sleep with once and then hang out with sans sex considered an ex? If so, I have a shitload more exes than I ever realized.

Aug 29 11 - 6:24pm

And P.S., for all the people that are up in arms over this woman not returning this guy's short story: If someone revealed the extent of my ho-bag-ness to an entire restaurant, I would destroy his entire goddamn ouevre with impunity. That is some fucked up shit to do to a lady, even one as slutty as myself.

Aug 29 11 - 8:34pm

I respect enormously you for introducing "ho-bagness" into this discussion. XOXO.

Aug 29 11 - 9:45pm


You are too funny.

Maybe as a sign of largesse, she could have returned it.

Aug 30 11 - 12:13am

Once again, a well written, funny story. Love the last line.

Aug 30 11 - 12:27pm

Great article! You had me from the start. We all have missteps in our dating and relationships. The key is to learn from those things and apply them to future relationships, as I think you illustrate quite well.

And not giving back the short story? That's no big deal. If you'd published it, that's be a whole other thing.

Aug 30 11 - 6:12pm

Please, please, *somebody*, turn this into a rom-com (or would it be an anti-rom-com?) in which no one gets the girl in the end but we all get that lost condom moment and the line about the pliers and the Albee dinner. Please! I find the dynamics of the friendships and flings here to be not only fascinating (he wasn't the least bit angry with KEITH? KEITH didn't get accused of "cold-hearted fucking" during a restaurant spectacle?!) but right on. Well-done, you!

Aug 30 11 - 6:39pm
Third Wave Housewife

I met my current partner, who I love like fucking mad and with whom I live and suspect I will spend a very, very long time (I am not fond of saying we will be ~2gEtHeR 4eVeR~*) because he watched his housemate crash, burn, and blow it with me. I had been pursuing the other dude to no avail (despite the fact that mutual friends gave him endless shit about getting in his own way and refusing to let it happen) and was letting it go when he embarrassed the hell out of me in public and refused to apologize and did a whole bunch of other childish, obnoxious crap that I very, very grudgingly was going to forgive (not without giving him hell first, though! I had just agreed to resume civil interaction if he gave me a few days of silence to cool off, in contrast to the week I spent waking up to groveling, pathetic text message novels that amounted to "I'm still not going to apologize and you should still forgive me because I am miserable at having fucked this up") and then his housemate contacted me. Like in your story, the original guy never got mad at his housemate but gave me passive aggressive shit for a week. He found out that I was seeing his housemate when he walked in drunk as hell in the middle of the night to us watching Let The Right One In on the couch...and then I didn't leave until 7 AM.

Sep 01 11 - 2:52am

Great writing, I will now follow you on the Twitter and more than likely purchase your novel. If you remind me on Twitter when it comes out, of course. I wonder what Bob thinks about this article?!

Sep 01 11 - 9:34am
Tommy W.


Oct 02 11 - 12:31pm

Oh Hi, Mark.

Sep 02 11 - 11:40am
My fav Line

"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."

Loved this line, lovely...

Sep 02 11 - 2:42pm

Thank you. All the best!

Sep 02 11 - 1:05pm

Re: When you can start seeing friends of an ex- (even a one-off), is like trying to decide when you can start making jokes about a horrific tragedy. Some people seem to be able to do it the next day, while others won't get over it for over a decade. I think it's best to play it safe by not going with a friend of an ex- until such time as that ex- has hooked up with someone else. At least then they won't have any excuse to get upset.

Sep 02 11 - 4:30pm

Litza, finding myself amused at the tenor of the replies.

But that's a GOOD thing, eh? The only bad review is the one not written, the only bad comment is the one titled "yawn."

I for one think you likely did the boy Bob a favor destroying his document. Hemingway, in "A Moveable Feast" describes a moment when his wife inadvertently loses a trunk full of his early writing in a train station, never to be found again. At first devastated, he realizes that it was probably the best thing she ever did for him, and encourages as a cure-all tonic for all new writers to lose a trunk full of their early efforts.

On another note, to this day 20 years later and to my grave a kiss with the ex of a friend of mine. A kiss to remember for a lifetime. A perfect kiss. Her casual and seemingly non-reasoned disengagement following a perfect kiss has been an enigma for me. Because she felt it too.

Go figure, eh?

Sep 03 11 - 10:35pm

You are funny as hell!

Sep 08 11 - 4:03pm

In my opinion, sleep with my friend (hurts - oh well) but gimme back my story!!