Love In A Red Box: The Unexpected Heartbreak Of My Friends-With-Benefits Fling

Long Reads is a bimonthly feature, showcasing long-form essays. 

I glance over at the packages in the mailroom. When I see his address, I instinctively reach for it. "Plated"? What’s this red insulated box? Food for two. Pre-portioned. Carefully curated. 

We lived together for years but never dated.

"He never wanted you, I remind myself.  I place the box down at the edge of the counter and walk away."

My neighbor and I started hanging out shortly after we found each other on the board of our NY co-op. The only two under forty, we traded glances when the older members ranted about noise complaints and where to place air conditioner sleeves. We instantly found a kinship, even a flirtation. At first I ignored his advances. He seemed young.  Awkward. Maybe I was misreading his cues.

We were both teachers on similar schedules and often ran into each other in the elevator, on the way to work, or in the street on weekend afternoons. These encounters were so frequent it was beginning to appear as if we were planning them.

When we were first becoming acquainted he’d email me for what I believed were bogus reasons: 

My computer charger is broken — can I borrow yours?

Do you have the super’s number?

And then it turned into...

We should meet for a drink.

I was surprised he was so forward but glad he finally made a move. I wanted to go, but I knew my pattern. I thought it best not to get drunk and make out with my neighbor. I was working on building relationships, slowly. Instead, I parlayed it into playing tennis. We’d find love on the court if it were meant to be. It was that simple.

The next day, excited to finally have a tennis partner, I emailed him all sorts of options of where we could play. This is such a healthy way to start a friendship, I thought. But he always cancelled.

He was sick. He was busy. Each time assuring me – he was 100 percent in. I began to get discouraged.

Then he emailed me.

I just got back from golf. Really sore. We should give each other massages. I’m really good. 

Now normally, I would press delete and move on, but something in me felt different. It was a holiday weekend, which for single people amplifies our soloist lifestyle. I texted a friend for advice but no one was around. Screw it, I thought. Why not have some fun?

Just chillaxing. Come on over. I replied.

Within a few minutes he was in my apartment, rubbing shoulders and kissing. 

“I’m a few years older than you, do you have a problem with that?” I asked, sessing out our relationship barometer.

“Um, well how is this any different than a one night stand?” He casually replied.

My heart sank. I’d never felt so used. One night stands were drunken connections — this was a man I knew, who I saw every day.

It was 4:00 o’clock in the afternoon – how the hell is this at all like a one-night stand?

Confident Elana would’ve shown him the door. But I was no longer that woman. I had been dumped so many times in the last few years I didn’t know who I was anymore. I so desperately wanted to be connected to someone. And so, I turned to him and said, “I guess my age doesn’t matter,” and continued to fool around.  All the while feeling like a part of me was breaking inside.


I found myself impossibly attached and addicted to his texts. He wasn’t ignoring me. He still wanted to play tennis; maybe I just had to be patient.

I kept on dating other men, putting myself out there. One afternoon after a horrible date (one of many) where the guy actually didn’t talk to me at all because he was too busy playing ping pong, I was feeling hopeless. Then I saw my ever-smiling neighbor on our tree-lined street. He went in for a bear hug and I found my head resting on his shoulder. This felt so much better than Internet dating.

I invited him up for a beer. He sat next to me on my corduroy couch and we talked seamlessly for at least three hours that day. Me about my crappy date and him about everything that was going on his life. I felt a real connection. Could we take it to the next level?

Later that afternoon, after a run, he handed me a bouquet of lilies wrapped in lavender paper he tucked behind his back, and I gave him a big sweaty hug. I read the card, written with care in calligraphy letters. He thanked me for listening and promised me my day would get better. He revealed later he'd only ever given flowers to two other women, and one was his mother. I knew then, this was getting real.

Within a few weeks, he had a permanent slot on Saturday afternoons, where he’d come by and I’d try to win him over with tasty delights.

Homemade french toast with raspberry compote, fresh brewed coffee made with three distinct beans, hearty pasta salads with fresh herbs.

I thought perhaps the adage was indeed true, that the best way to a man’s heart was through his stomach. He had an ample paunch to fill, so my shopping began to increase. I even began making weekly trips to the farmer’s market to get whatever was in season. I liked being able to focus on someone else and he relished in the attention I was giving him.

"I was sustaining on only a ration of love. I wanted more."

After a while, he just came by whenever. He even had his own set of keys for emergencies, but some days he would just chill in my apartment when I went away. My place was homier with more perks: cable, printer, free wifi, and his favorite Japanese beer chilled in the fridge. Sometimes we’d break bread together. I didn’t cook for myself but for him it felt natural — nurturing, even — and I did so with pride. Sometimes we’d go out and laugh endlessly, and I wondered why all my other dates were so painful and ours so natural. I wanted to get closer to him but I did not know how. 

We were spending more time together and in constant contact. Every time my phone would beep I would get excited — a Pavlovian response.

Every time I’d get encouraged, he’d talk about another girl he liked, or someone he was dating, and I felt an imaginary knife swoop in and out of my body. 

I thought our Saturday sessions would satiate me. Once a week was enough to get attention, but also not enough to get closer. I was sustaining on only a ration of love. I wanted more. I’d invite him places, parties, etc. and he’d always find an excuse not to go. And just when I would start to move on and date other guys, he’d email a sweet message and text when good news came his way. I knew I was special in his life and I thought it was time to tell him my true feelings. Maybe if I did, he would finally start dating me.

“I don’t want to be your friend, I want to be your girlfriend,” I stammered.

He kissed me on the forehead and said, “I don’t want to date you.”

“I would break up with you,” he said. “But we aren’t even dating.”

I didn’t think I could feel such pain. It didn’t make any sense to me. He wanted a girlfriend so badly, and there I was pouring out my heart, feeding his soul — and all he wanted was a better option. Just like all the other men.

We agreed to give our friendship a break. One month, no contact. I felt like a part of me was missing.

I tried to be strong, rid him from my life, but I missed him more than I could bear. We slowly became friends again. We couldn’t help it, we were so used to being in each other’s lives – so close in proximity. We became closer than ever.

One afternoon we were hanging out in his apartment for a change. I brought up fresh salad for us to nosh on. I noticed a pair of black heels on the floor. “I’m surprised you didn’t say anything earlier,” he said.

“So you have a girlfriend now?” 

“Well, she lives in another city,” he continued. I felt relieved. No way this one could last. But it did.


She lives in our building and has been here almost two years. She’s in her twenties, wholesome looking, thin and polite, a Midwestern girl — the total opposite of this brash, curly-haired Brooklynite. I cringe every time I see her and she politely holds the door open for me. I’d move out if I could afford to, but NY real estate leaves me few options.

Every Monday their box arrives in the mailroom. Like clockwork. The dinner they will prepare together, sustainably caught, sourced organically. Minimal work.

Some days I take the cardboard cube firmly in my hands. First, I turn it upside down. Then I shake it like a piñata, hoping the scraps of food will fall out of place. I know this is irrational and I hate that moment of clarity, when I can see my own irritational impulses reflected back so clearly. Who is this woman about to smash a box of tepid food? He never wanted you, I remind myself. I place the box down at the edge of the counter and walk away.

While food and friendship brought us a certain type of closeness, it was never anything more, no matter how hard I tried. He made his choice. Young. Uncomplicated. Easy to order. So I turn the box upright and grab my mail and go to my apartment. Taking the stairs three flights up, no longer wanting to run into him. No longer wanting him in my life.

I pretend it doesn’t bother me. Because that’s what you are supposed to say. That you are strong and fine and don’t need him anymore. And I don’t need him. I just miss him — my weekend friend. The one who brought me soup when I was sick or sent me cards when life got tough. The one I could talk to for hours about nothing and everything. I haven’t found anyone else since.

While I don’t know much about their relationship, I do know what they eat – at least on Mondays. It is perfectly portioned and freeze dried for two. Two lovers who mix the ingredients together and dine in a way we never will.

Time has passed and they are now engaged, and I have finally learned to let go of both the love and the friendship. I’m not sure I like who he has become. It’s hard to understand why I held on so long. When I was with him, I honestly thought I was getting closer to someone; it is only now I realize I was getting farther from myself. It is time I get back to her and make room for someone else at the table. 

I still scan the mailroom for packages. Some habits die hard. This time I notice a new one, "Sun Flower." Even they have moved on to a new box, the latest trend in online deliveries. I leave the package unscathed and proceed up the stairs, no longer envious of love in a box. I too have moved on.

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