Do Not Plan a "Last Night Ever" With Your Ex


After Colin* dumped me, we continued to hang out for weeks. It wasn't your typical breakup — we'd only been dating for a month and a half before he decided to end things. But immediately afterward, whenever I saw him, I'd say, "It feels weird not to kiss you," and we'd end up kissing. Often, that would turn into sex.

Eventually, I knew we couldn't keep going on this way. Coming over to his place to cuddle and kiss and hang out was couple behavior, and we were no longer a couple. Still, we kept on having sex, because if I was at least having good sex, I could justify hanging out with him, I reasoned. Otherwise it just felt like unnecessary emotional agony.

So over text message, I proposed we have one last romantic night together.

"We can have mad unprotected sex, cry together, you can make me come a bunch of times. And that's it, we're done," I wrote. "Then I'll be out of touch for a month or so and things should be fine between us."

"Honestly, the whole idea of that makes me feel sad and entirely un-horny," he responded. "But I'm in."

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"If tomorrow you won't be mine/ Won't you give it to me one last time?": Other people have attempted to have romantic last nights with their lovers before they call it quits. The concept has appeared in pop culture here and there. There is One Direction's new ballad "Love You Goodbye," where the boys sing "If tomorrow you won't be mine/ Won't you give it to me one last time?" In "All I Ask" by Adele, she sings "If this is my last night with you/ Hold me like I'm more than just a friend." So I'm not the first to try to attempt to make a difficult thing (a breakup) more romantic, and maybe even a little more fun.

In theory, at least, having a last night with an ex is a sweet idea. When I asked Michele Kabas, a therapist and licensed social worker, what she thinks of planning out these sorts of "last nights" she explained that while she hasn't frequently come across these scenarios, "there is never a right or wrong across the board." But she cautioned that for many couples, it can only cause unnecessary pain.

"Getting together in [a romantic] way defeats the purpose [of why] you were breaking up," Kabas said. "It just prolongs the agony."

Kate*, 22, told me that she attempted to have a romantic last weekend with her on-again, off-again boyfriend of two years, Jared*. "I realized I needed to say goodbye to him for good," she explained to me.

At that point, Jared and Kate were each living in different cities in Europe. Kate was adamant about breaking up for good in person and she wanted to do it ASAP.

Kate didn't tell Jared about her plan to have one last romantic weekend with him, so he didn't know what he was in for. "I didn't mean for this to be cruel. I just genuinely wanted one last romantic weekend with him," she explained. "This is really sick and twisted, but I had just splurged on a lot of lingerie and wanted to wear it for someone."

Unfortunately, when Kate finally met Jared, she was wearing some of her sexiest lingerie underneath her clothes. As they began to have sex, Jared's phone went off and he picked it up. Kate started to remember why she didn't want to be with Jared in the first place (because he prioritized his job over their relationship) and why this weekend would not work.

"We had a lot of angry sex," Kate said. "It was the worst weekend of my life. Obviously I would never pull any of this shit again."

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Shawn, 27, also had a last romantic weekend with his ex, Karen*. They broke up two weeks before an already planned weekend trip, so they decided to go anyway. "It was Karen who framed it as this being our final time together as a couple," Shawn explained. They'd been broken up for two weeks, but as soon as they got to the hotel, everything went back to normal.

"We ended up having sex as if this was our first trip together, not our last," Shawn told Mic. "It just felt so intimate and revealing and new."

Because they had had such a good time on the trip, Shawn and Karen tried to be friends when they got home. That's when everything fell apart. Karen cheated on her new boyfriend with Shawn, and their toxic relationship continued for far too long.

"When I look back on that trip, I really just wish I could've appreciated it for what it was — a clean break — and then walked away," Shawn said. "Instead, we ended up dragging things out for another six months — with our last moments being toxic, damaging and angry."

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"If this is my last night with you/ hold me like I'm more than just a friend": As my last night with Colin approached, he began to have second thoughts. I told him we should meet up regardless. 

"You're not obligated to have sex with me," I told him. "But we should still, at the very least, talk."

"Definitely," Colin said. "Come over."

Colin asked that we go to a small gathering at his friend's house because he was having a rough day. I acquiesced and agreed to accompany him because I was afraid he'd cancel on me if I didn't agree to go. I knew we were already broken up; I shouldn't have felt afraid of him resenting me, but I couldn't help it. I still wanted Colin to like me. I still wanted Colin to want me. 

Things weren't going to be as neat as I wanted them to be, but I accepted my fate and we trekked over to his best friend's house. As I was hanging out with Colin's friends, I began to feel this fiery rage overcome me. "Why am I here?," I wondered. "Why am I at my ex's best friend's house right now?"

When we finally got back to Colin's place, I began to yell at him for the first time in our relationship. "Why the fuck am I here?" I said again and again. "Like, seriously, what the fuck do you want with me?"

"I really care about you," Colin said. He started sobbing. "I'm just such a mess right now. I'm really sorry." 

"It's going to be okay," I told him. "It's all going to be okay."

"I don't think it is," he said.

"Would seeing my boobs help you feel better?" I asked.

"Yeah, it actually would," Colin said, smiling. 

Off came my shirt, and as Colin groped me, the whole thing began to feel farcical. We stood together in front of his mirror — me, topless, and both of us red-faced from crying — and Colin hung his arms around my waist. It was a nice, tender moment.

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"Last dance/ the last chance/ for love": Colin and I tried to stay friends for about a week, until things abruptly started falling apart. I started to feel trapped by him, like he had a psychological hold on me, even though I knew I was the one encouraging the bad behavior because I kept initiating the post-breakup hookups. 

After one final drunken argument, I told Colin he needed to stop texting me. "Every time you contact me, it hurts," I told him.

I wanted to have a nice last night with Colin because I wanted to hold onto the nicest parts of our relationship: the physical intimacy, the sex, the occasional tender moments. But I realized I couldn't do those things with him. After we broke up, I realized we could have as much sex as we wanted, but that didn't change the difficult truth that he just wasn't that into me.

Breakups are never fun or easy, and when you try to make them that way, it always seems to backfire. Whether you're immediately trying to be friends post-breakup or trying to plan out a sex-fueled last night, it just doesn't work according to plan. Our desire for these clean breaks speaks to our need for "closure," which is, more or less, a made-up term. Often, we don't need closure; we just need space from our exes and more time to heal from the hurt they caused us.

"Every time you contact me, it hurts."

Still, when planned meticulously, a romantic last night can assuage the pain of a breakup. After Cecily*, 23, and her long-distance girlfriend had a messy breakup, they decided to meet up a few weeks later. The first night they hung out, they had sex and the night ended in "a whole bunch of crying," Cecily told me.

A few days later, Cecily suggested a romantic "last date" so her ex's visit wouldn't end on a sour note. They had a nice lunch together and as they walked back to Cecily's apartment, they held hands and listened to romantic songs. "We kissed, but just once, and then she left," Cecily explained.

Ultimately, Cecily has fond memories of the end of the relationship, in large part because they had the chance to spend that last night together. By making the last night something not focused on sex, she was able to begin to see her ex in a new light: as a friend.

"Instead of ending our relationship with a messy, emotional hookup," Cecily said, "we were able to cap off a pivotal relationship for both of us with a positive memory."

*First names have been changed to allow subjects to speak freely on private matters.