On the Difficulty of Trying to Casually Date Your Best Friend and Ex-Boyfriend of Five Good Years

when-harry-met-sally-originalIt’s not quite 7 am on Monday morning, and I’m shuttling my coffee cup into the car, alongside my massive red binder which is full-to-bursting with student essays, half-graded, and my beat-up, beloved red handbag. The sun’s not even up; in fact, it’s misty, and gray, and as such, I’ve donned my hooded London Fog raincoat– also red.

I slam the door, and start the car; the Sirius radio display pops up: “September Morn,” by Neil Diamond, on the “Love” channel. “Oh, FUCK OFF, Neil!” I bellow, and turn the dial to Morning Edition, immediately soothed by Steve Inskeep’s voice. Neil Diamond was “our thing,” lo these last twelve years. When I went to Paris in 2001, I brought him back an original vinyl of the soundtrack to Jonathan Livingston Seagull, and we displayed it in our apartment: Neil, in his aviators, staring out at the gulls circling the sea, with a candle, on a speaker. Whenever “the Diamond” came on Sirius, I’d take a picture of the display and text it to him. Or Prince. Or any number of the dozens of musicians and bands we’ve mutually obsessed over for more than a decade, now.

I’m a heartbroken, monochromatic hot mess.


To paraphrase Elliot Smith, everything reminds me of him. Even writing this, I recall putting that raincoat on in front of him for the first time–

“You like?” I say, doing a little twirl, raising my eyebrows.

“Yeah, a lot,” he says, eyeballing me. “You look like, I dunno, like Red Riding Hood meets Ilsa from Casablanca.

“Then my evil plan is working,” I reply, and strut out the front door to wherever we were going. Lunch, probably. That was our thing. He works nights, I work days. After a while, we settled into a routine– Mondays and Wednesdays I had the afternoons free of teaching. We’d eat at one of our favorite holes in the wall– Pho or Mexican, usually– and come back to my house and fuck and lie around and listen to music and goof off. He’d leave for work; I’d scramble to grade something, or jog, before getting my son from daycare.

We wanted to write a screenplay together. That’s what the lunches were about– a pretense. Last fall, he finally cut the cord with his longtime girlfriend, a person I am fairly sure forbid him from seeing me, although, of course, he never listened, and lied, and saw me anyway. I mean, it was innocent. Ok, it was innocent with two exceptions– in the fall of 2009, shortly after I left my husband, we went out for drinks at the Irish Pub. After, he drove me home, and kissed me good-night– swiftly, with an open mouth, and a ferocity which surprised me. Later that year, a week before Christmas, we went out to the same bar, and he brought me back to the apartment they shared. It felt totally wrong. She had an entire bedroom devoted to her shoes and dresses, and her thong underwear, in a variety of colors and fabrics, was strewn from one end of the place to the next. At the time, she was 24, and I was a month from 30– I remembered being that age, that girl, obsessing over my shoes and clothes, painting my eyes six dozens shades, garish blues and pinks and chartreuses, living, in fact, with him through it all. A lot can change in six years. That night, when he picked me up, I was dressed in jeans and a beat up old flannel, a pair of knee high boots I’d had for half a decade, and yet I’d never felt more confident, sexier. As I got out of the car, and walked toward the bar, he said, behind me, “Nice ass, sister,” and I thought, He’s still in love with me,and grinned, and rolled my eyes. “Thanks,” I said, over my shoulder. Anyway.

At their apartment, we drank Amstel Light and listened to Otis Redding and D’Angelo, Angie Stone, all the records we fell in love to, used to make love to. We talked for hours about our failed, but lovely, relationship. We were still, I realized that night, what we’d always been– the best of friends who liked having sex. There is a section of Nick Hornby’s famous book High Fidelity that talks about how important it is in a relationship that the two people like the same things– this is where we always worked like clockwork. The same music, the same movies. The same fashion. The same places, the same people. He loved my family, they loved him. When we finally split for good, I knew whoever I ended up with would never have a mother like his: a beautiful, old-school, spitfire Southern belle who spoke Greek with a low-country accent and usually had a hot pan full of something scrumptious in one hand and a cigarette in the other. We were, mostly, ideal for one another. Just young and restless and stupid.

Or, at least, I was those things.

That December night, we didn’t kiss. We held each other, and he ran his hands up and down my back. We both cried. He told me he had never stopped loving me. I told him the same. We talked about being young, and restless, and stupid. I felt patient, and achy, and desirous of what I knew was impossible. The next morning, his girlfriend would return from her parents’ house. In a month, I’d meet and fall head over heels for my son’s father. When we left, it was nearly 4 am, and snow had begun to fall in fat flakes; by morning, there would be two feet of it.


This past fall marked the first time since we broke up that the two of us were single again at the same time. Hence the lunches. First, of course, it was cocktails, followed by a preliminary conversation in the front seat of his car.

“So, well, the thing is… I always want to kiss you,” I said. “No matter what, or when, or who else we’re both with, I always want to kiss you.”

“I know,” he said back. “Me too. But I don’t want to just get back together, to just fall back into our thing–” 

“No,” I said firmly, shaking my head. “That’s not what I want, either. It’s so different, now. I have the baby, and I’m so busy with writing and teaching. I don’t have time for a boyfriend. I don’t want one.” I sounded very convincing. I even believed myself. After all– I meant it. At the time.

“And I DON’T,” he said, equally firmly, with a slight edge to his voice, “want to just be another guy on your blog, Z or J or Q or whoever the fuck.”

“So what, I can’t blog about you?” I asked, poking him in the ribs.

“Well, I didn’t say that.” I had to laugh– one thing every man I’ve written about here has in common– I’ve cleared it with all of them, first, and they all say the same thing– “Oh, write away, you can use my real name, even.” I suppose the content dictates that decision. No one has yet protested my decision to publicize their prowess in the sack.

And so, preliminary discussions turned to kissing, which turned to necking, which turned to him popping over after work (bartending– I know– I have a penchant for them), which lasted most of November and December. No sex. Lots of snuggling, lots of laughs. A picking up of our old, cherished rituals– tucking my leg inside of his when we spooned, an uncanny ability to reference and quote When Harry Met Sally at least thrice in every conversation we had. We broke up officially in 2005, but we had never fallen out of touch. It was easy. Ridiculously so. No strings, all fun. No stress about texting him at any hour, or calling him to gab randomly– I would have done it before, and hey, nothing was different, now, right? We were best friends who canoodled. I asked him to my sister’s wedding in May; he accepted. The fall semester wound down.

Then, the night before the last day of class in December, my son, having just that morning seen the doctor for a mild cough, sitting in the bathtub on a Sunday afternoon, began to suddenly shake and turn blue. I grabbed him and frantically called an ambulance. He was rushed to hospital, stabilized in the emergency room, then admitted. We spent a full week in the pediatrics ward, where he was tested for everything from meningitis to Kawasaki disease, until he was finally diagnosed with atypical bacterial pneumonia in both lungs. I didn’t see the light of day for that entire week, and almost everyday, he was there to sit with us. My best friend. My ex. My sort-of lover. My best friend. Texting me hilarious stories and links to great songs while the baby slept, his poor body wracked with fever, holding my hand while I dealt with one particularly inept doctor who wouldn’t look me in the eye, choosing instead to fiddle with my son’s “Doc Ock” action figure while he mentioned the possibility of a diagnostic spinal tap, and blamed any difficulties we had on the exhausted, overworked nurses. At night, I would fall into reveries, imagining us traveling together in Spain, the South of France, eating delicious things, making up for lost time. When we got out of the hospital, I realized I was in love. Again. Or still. Or some oddball combination. It seemed imperative I tell him as much. Which, of course, I did, being me, and incapable of keeping feelings to myself.

He looked a little like he was going to throw up.

There was much talk of “needing time” to get over his past relationship, which had only just ended in October. There was much talk of wanting to continue to see me. To get to know me, “now.” I agreed these were good things. My heart sank. I badgered and bullied him into admitting he still loved me. That he always had. He did. He admitted it. I threatened to walk if we didn’t make some kind of commitment. He begged me not to take my friendship from his life. I cried. He cried. It was a mess. I told him the truth: I wanted to get married. I wanted to have babies. I wanted a house with a fence. I wanted to do the things we should have done back in 2005 when we were young and reckless and dumb and selfish. He said he wanted those things, too– maybe. Down the line. He needed time. I said I would try to give it to him.

And– ugh! I tried. I tried really hard. I did a halfway decent job, at least for me. I am so impatient, so impulsive, a big stupid heart with feet. When we finally slept together, it felt brand new and fun. “Was it always this good?” I asked him.

“It was always really good, but, ah, yeah. Wow.”

Marie Howe writes in her poem “What the Living Do,” “We want more and more and more and then more of it.” This accurately summarizes my difficulty. When someone like this comes back into one’s life, when it’s everything good it was in the past, but better, now, because you’ve grown up, you have your own life, your own world, a job you care about, passionately, and you feel able to share those things with that person– well, how could you not want more and more and more and then more of it? How could you want anything else?

The last time we saw one another, we ate sopes and tacos and he told me how beautiful I looked. Back in my room, we made love, and listened with a strange combination of amusement and terror as a dozen men removed a giant, dying tree outside my window. “Do you know the song ‘Skylark,’ by Johnny Mercer?” he asked.

“I don’t think I do,” I said. So he played it, and I realized I had heard it, just didn’t know the name. Later, I discovered Mercer had penned the lyrics for Judy Garland, who he was in love with, but couldn’t have: “Have you anything to say to me? Won’t you tell me where my love can be?” “I’m writing you a poem,” I texted him while he worked.

“Oh yeah?” he wrote back.

“It’s called ‘Skylark.’ ”

“That is so, so, SO cool.”

I haven’t seen him since.


The problem was me. As ever. After almost six months of being friends with benefits, I panicked. All the crappy insecurities I’ve felt with other men, but never him, kicked into overdrive. If a day passed without us talking, I worried he was over it. And truthfully, I was making more of an effort– doing most of the calling, the planning, amending my schedule to suit his. I wanted something firmer. Were we dating? Weren’t we? What were the chances we would, sooner rather than later, be something more official? “I can’t do this,” I told him.

“Neither can I,” he said. “I’m not ready. I love you, I’ve always loved you, I’ve never stopped. But I can’t do it.”


That screenplay– the one we never got anywhere with. Well, it was my idea. A pretense. A way to keep him fascinated, guessing– Love ME, dammit, my heart is always bellowing away. We wanted to write a hip romantic comedy, something intriguing and smart, more Charlie Kauffman than Meg Ryan. “What if,” I texted him, as I readied myself for mass on Christmas Eve, knowing I’d see him that night, thrilling at the prospect, painting my lips scarlet, rolling lacy tights over my newly shaved legs, “we wrote a romantic comedy about two exes who are the best of friends, who are writing a romantic comedy together?”

“You’re a genius,” he wrote back.

A week later we lunched at our favorite Vietnamese place– steaming bowls of Pho, exclaiming over the broth, the way it tastes almost transcendent– more than the sum of its parts. “If I were writing a screenplay,” I said, “this scene would go in it. Old lovers playing footsie under the table, freaking out over how delicious this soup is.”

“I could bathe in this soup,” he said, blowing carefully on a spoonful.

And there we are, frozen in time: two old lovers, rewriting our story in our weird, collective head. The camera zooms in on the steaming bowl of soup, and we are there, in miniature, spinning wild circles on sliced jalapenos, diving headlong into what tastes good, feels good, is just, simply, always right– delicious food and delicious conversation with the person I’ve grown up alongside, careless, reckless, timeless, lovelorn, laughing, laughing, laughing. A boy who loves a girl who loves him back. Just like the movies.

This entry was published on April 28, 2013 at 3:28 pm and is filed under Uncategorized. Bookmark the permalink. Follow any comments here with the RSS feed for this post.

2 thoughts on “On the Difficulty of Trying to Casually Date Your Best Friend and Ex-Boyfriend of Five Good Years

  1. Oh, Emily. That is all. Just, Oh Emily.

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