7 Harsh Truths I Learned From Sleeping With My Ex For Two Years

Heartbreak, Sex

My ex and I broke up in one of those super-dramatic ways that you'd expect to see in cheesy romantic comedies that we all love to hate. Short summary: He couldn't give me what I wanted emotionally, and even though I probably loved him more than any of my past boyfriends combined, I knew that settling for a half-hearted love would never be enough for me in the long run.

So after handing him his key back at a sushi restaurant while 'If You Don't Know Me By Now' played in the background, I stepped out into the rain, hailed a cab uptown and cried my eyes out. I wish I was kidding.

A week later, he was whispering he loved me in my ear while going at it from behind so hard I orgasmed twice.


I assumed our post-breakup sex was a one-off that we both needed to seal the end of a relationship that had become so tainted it couldn't last, but I was wrong. Over the course of the next two years, I continued to sleep on-and-off with my ex.

At his place. At my place. At his mom's house. In the stairwell of my apartment building. In his car. After a really bad date with some other guy. After a 5K race, while we were still in our sweats. On Valentine's Day. On New Year’s Day. In the shower, on my birthday, after I slept with someone else on his birthday.

We had more sex in the two years we were broken up than when we were together.

It may sound ridiculous, but I don’t regret any of our encounters. In those two years, I learned a lot of surprising things about love, sex, myself, relationships and most importantly, how to let go once-and-for-all. Let me let you in on a few...

1. He kept me from being slutty.
My ex and I never had a problem in the bedroom. If anything, it was the place where we really worked. We could switch between intimate and loving to dirty and kinky on a dime. By sleeping with him after a bad date or on a random Sunday afternoon when I desperately wanted to rest my head on a man’s chest, I called him instead of a random guy. While I had short relationships in those two years, I mainly only slept with my ex.

2. He reaffirmed what I wanted.
After my ex and I had sex, we would try to have brunch only to end up fighting over the same 'ole things we always fought about. My relationship with him affirmed what I had suspected (and why we had broken up) in the first place: I need a healthy sex life AND healthy conversation with my future husband. My ex and I mastered the first, but when it came to the hard, real-life topics? We couldn’t make it past the first mimosa without one of us getting upset. 

3. He made me really cherish my friends.
When I'd disappear for a day or leave early from the bar on a Saturday night, my friends knew I was likely getting naked with my ex. And even though I witnessed a couple of eyerolls, they stood by me. Every time I'd cry over him or express my frustrations, they'd calmly and patiently tell me that I was better than being his sloppy seconds and encourage me to stop. It didn't matter how often I went back to him, my girlfriends were there for me. (They also knocked some tough love into me, which eventually helped me kick the habit.) Since then, I've had other friends go through the same experience, and though I desperately want to tell them to let that man go and move on, I understand and I'm a better friend for it.

4. He made me pickier about my next boyfriend.
Even though my ex mostly had good intentions, he had a lot of growing up to do, despite being eight years older than me. He was insanely selfish and our relationship was always on his terms. He always had one foot out of the door and no matter how much I reached for it, I could never get a firm grasp on his heart. Beacuse of him, I'm harder on guys that I date now, but it's simply because I refuse to let lackluster be good enough.

5. He proved how much love I have to give.
After we slept together on a work night, we were getting ready together in the bathroom when I peeked around from the shower curtain and asked him what I taught him. (I subscribe to the notion that each person we date is supposed to teach us something.) His answer was simple and it stuck with me:
"Linds, you taught me how to love." What did he teach me? How to not waste my love on someone who can't give me what I want and deserve. And that love is much better than sex.

6. He made me go a little easier on myself.
Let's be real. There's no sugarcoating the fact that sleeping with your ex isn't the best idea. I knew I was selling myself short and letting comfort rule over being smart. But at the time, it felt like what I needed. Knowing I was making a bad choice, yet allowing myself to make it, taught me to be a little kinder to myself. Because it's not always as easy or straightforward to do the thing you know you should do. Sometimes, you gotta go with what feels right in the moment. Until of course, it doesn't anymore...

7. He showed me how to recognize when a relationship is really over.
The last time we slept together, we ordered in sushi and he brought over a bottle of my favorite red wine. We watched TV with one eye on one another’s lips, and one thing led to another. We had sex in the living room, the kitchen and the bedroom, before taking a shower together. And though we slept in the same bed, I didn't sleep at all. Nothing had technically changed ... yet, everything had. I could just feel it. The next morning, as we drank coffee and watched the morning news, I realized it was sincerely, completely over. The hunger between us had left, along with the passion. We were in different places now. We wanted different things. Mostly, we wanted better love. And just like that, we never slept with one another again.


While that ending was less dramatic than the first one, it was the real ending. It was when we both let go of one another without saying anything. Because we didn't have to. We both just knew. We've talked occasionally since, and though I don't have a desire to be with him or share my bed with him, I feel no hostility or anger toward him. He's moved on and so have I. It just took us a while to get there.

I wouldn’t recommend sleeping with your ex for quite as long as I did but don't beat yourself up for giving into the temptation a time or two. Or ... a dozen. If you let it, doing something 'wrong' can teach you a thing or two and it might even heal you. And know this: whatever—and whoever—is next will definitely be stronger. Because sometimes you have to make the same mistake over and over again to learn how to cherish something great.

Lindsay Tigar is a 26-year-old single writer, editor and blogger living in New York City. She started her popular dating blog Confessions of a Love Addict after one too many terrible dates with tall, emotionally unavailable men (her personal weakness).


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