Sleeping with the Enemy

Part II of my Saga with Max (or, why sex with an Ex is always a bad idea)

Back in late April, I wrote my most personal story yet, about going through a breakup during Covid. A breakup that left me feeling even more depressed and alone than the pandemic had already made me.

If you haven’t read my initial post about Max, you can do so here.

I was nervous to put my story out there, particularly since it was so deeply personal, but I got such a fantastic response from readers. And a good majority of the comments were about how I was better off without the guy in question.

Unfortunately, I didn’t see it that way at the time, and our story didn’t end with the pandemic dumping.

*Note: Names have been changed, as always.

☆ ☆ ☆

The Guy

Max and I met online – I had just gotten out of a serious relationship with Brad while Max was a few months shy of getting out of a marriage. At the start of the relationship, he’d made it clear that he wasn’t looking for anything serious right away – and neither was I.

But, I developed very strong feelings for him and pretty soon, I was hopeful that we would become exclusive.

Looking back, I know I should have seen the warning signs that Max wasn’t ready (I mean, hell, he even told me upfront that he wasn’t) but I’ll give my (slightly) younger self a break here because, although he said he didn’t want to jump into anything, he also said he was open to a more serious relationship with me.

Quick side-note here to anyone out there in a similar situation: If a guy says he’s “open” to a serious relationship, it doesn’t mean shit until that “open to” becomes a bona fide reality.

Making Assumptions

But, again, I had feelings so I overlooked that reality and focused solely on my emotions.

I knew we weren’t exclusive, and while I went on other dates (and, knew, of course, that he did too), I wasn’t sleeping with anyone else. And, (somewhat naively) I assumed he wasn’t either.

Of course, that was a mistake that I’d find out about much later.

I’d like to pause here for a moment to give another important PSA – if you’re in a similar situation, please, for the love of god, don’t assume anything!

But assume, I did.

Meme about making assumptions

We were spending a good deal of time together – so much so that I wasn’t even sure how he had time to date other women – we spoke daily, and I’d met several of his friends. It certainly felt like a relationship to me.

So, we carried on in that semi-relational state for nearly six months.

The Breakup

Then, in mid-March of 2020, the entire world changed.

Covid hit and with it, I lost my job (technically, my place of work was just temporarily closed, but still – I wasn’t getting paid.) For the first time in nearly 15 years, I was left with nothing to do all day. Pair that with my tendency to become anxious in romantic relationships and it was a recipe for disaster.

The Impact of Covid

Within a few weeks of my job loss, there was a statewide stay-at-home order and plenty of social-distancing requirements were put into place.

Aside from my immediate family, Max was the only person I was socializing with in-person during this quarantine order.

Again, I assumed the same was true for him – I mean, it seemed only logical (once again, see the above note on assumptions.)

While this should’ve made me feel less anxious, it only served to increase my feelings of discomfort. I kept wondering, What will happen when the quarantine period ends? Will he go back to dating other women, or will he finally commit to me?

man and woman sitting on bench outside wearing covid masks

With all these unsettling thoughts swarming along with my uncertainty about work, I started to become depressed. And of course, I leaned on Max.

But, he wasn’t looking for someone to comfort or take care of – he wasn’t looking to be a “boyfriend” to someone, he was just looking to have fun.

So, he broke up with me, blaming it on a matter of timing rather than disinterest.*

*This would become important later on

Keeping a Spark of Hope Alive

The breakup left me utterly devastated. At that point, I’d not only fallen in love with Max, I believed he could be the one.

And it didn’t help that he ended things with me on a hopeful note.

He’d said it was due to “timing,” that he understood my anxiety and depression, but that he wasn’t able to be supportive of me. He was just getting out of a marriage, he reminded me, and he wasn’t in a place to commit to anything other than fun and casual dating. The fact that I’d started to lean on him more and more was decidedly not fun and casual.

No, now, we were veering closer to relationship territory.

All of that should have squashed any hope I had of reconnecting, but it didn’t. He said he still had strong feelings for me and threw in that he thought there was a chance for us in the future.

Staying Friends

I’ve always been one to try and stay friendly with exes, and Max was no exception.

So, after our breakup, I told him we could still be friends. And I meant it.

Of course, I was secretly hoping that this friendship would eventually lead to him suddenly realizing how much he loved me and come running back…

but that’s neither here nor there.

The Situation: Sex with an Ex

After a few uncomfortable post-breakup conversations, we did end up remaining friends. We still texted often and we got together a few times for lunch or coffee.

Then, one night, he came over to watch a show with me. And before you go thinking that this was an understood innuendo, we’d started watching Westworld when we were dating and we’d kept up with it in our breakup – only, now we watched the episodes separately while texting about it. So, him coming over for an in-person viewing wasn’t that unusual.

I’m sure you can guess where this is going, though.

Sex with an Ex

Somehow, we ended up in bed together that night.

It started with some innocent flirtation here and there, but soon, the show ended and yet, Max stayed. We made small talk, but I could tell by the way he was looking at me that he wasn’t staying for the conversation.

When he leaned in to kiss me, it felt 100% natural and suddenly, we fell back into our familiar carnal desires.

Afterwards, we cuddled for a minute or two before Max said he had an early meeting the next day. I walked him to the door where we kissed goodbye.

The Aftermath

The story could have ended there, a one-off ‘sex with an ex’ encounter. But it didn’t.

For the next few weeks, Max and I started to spend more time together, and each time we met up, we would fall back into bed.

Obviously, this meant a great deal to me. It fueled that spark of hope I’d still been holding onto. Now, I wasn’t so naïve as to believe we were back together, but I thought this new arrangement we had meant something.

Eventually, I worked up the courage to ask him.

A Second Round of Heartbreak
woman with dark hair sitting curled over ontop of her bed holding her stomach

One afternoon, I asked him what exactly we were doing, to which he replied something along the lines of, “I thought we were just having fun.”

Devastated, yet not entirely surprised, I tried as best as I could to hide my feelings.

And, in yet another mistake, I agreed to this new, more casual friends-with-benefits entanglement.

When it ended, it was messy – but the details of that fall-out are far too much for this post (who knows, I may need to make a Max Part III in the future).

And it left me even more heartbroken than it had the first time around.

Life Lesson

Don’t have sex with an ex. Just, don’t.

And for anyone who thinks their situation is “different,” let me just go ahead and reiterate that: DON’T HAVE SEX WITH AN EX.

Have any of you ever had sex with an ex? Let me know in the comments below!

As always, thanks for reading.


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  1. avatar

    Yes, I have and I would regret it after.

    1. avatar

      It’s never a good idea, I know.

  2. avatar

    We’re so sorry you had to go through this.

    1. avatar

      I am too, but it was a good learning experience.

  3. avatar

    I love the transparency and honesty with this! thanks for sharing

    1. avatar

      Awe, thank you so much! And thanks for reading xx

  4. avatar

    Thanks for sharing this post! It’s so honest and I think many people will be able to relate.

    1. avatar

      Awe, thank you so much! That means a lot to me and I’m glad you enjoyed it.

  5. avatar
    Alicia Thompson says:

    Hi girl, WOW this post is just… WOW relatable, truthful and HONEST. I can’t explain how much it’s a bad idea to get back with an ex but do we ever listen to ourselves until after it… nope! Thanks for sharing such an honest post. Alicia

    1. avatar

      Awe, thank you! And thanks so much for reading xx

  6. avatar

    Love how candid your post is! I’ve had a similar experience many years ago. We were together then broke up but just kept hooking up every now and then, I was given false promises and hope but it was all a lie. Thanks for sharing your story, it’s definitely one I think alot can relate to.

    1. avatar

      I think so many women have made this mistake which is a shame. But I’m glad reading it helped you!

  7. avatar

    Sounds like such an awful experience, but unfortunately I feel like a lot of people will be able to relate to this! Going back to an ex when it ended on really bad terms is never a good idea. Thanks for sharing x

    1. avatar

      It certainly wasn’t for me, but I hope that other people can learn from this mistake (or at the very least, find comfort in knowing that they’re not alone.)

  8. avatar
    Inna | ThatUnknownBlogger says:

    Ahh, dating or sleeping with an ex is a big no-no. I do understand, however, how you must have felt and I can’t imagine how you hide your feelings when the words ” I thought we were just having fun” came out. I just hope that you find a guy who doesn’t want to just have and actually want to be serious. Thank you for sharing your thoughts and experiences. This is some really personal things and yet you had the courage to share this. So, thank you!

    1. avatar

      In my head, I thought I hid my heartbreak well, but I’m sure he could tell how upset I was! Thanks so much for reading

  9. avatar
    Mind Beauty Simplicity says:

    ugh, this is why i always hated dating. all the “what are we’s” and the “i like you but i don’t want to make it official” bs….
    i’m sorry this happened to you. he clearly missed out on a great relationship. i’m sure you’ll move onto bigger and better things!

    1. avatar

      In a way, I am too, but it was also a learning experience and that’s always important.

  10. avatar

    I am very far from thr dating world. Married 25+ years.
    I appreciated your honesty in this post and I am sure many people can relate to this story.

    I hope you do indeed find “the one”.

    1. avatar

      Awe, thank you! And thanks for reading xx

  11. avatar

    It’s aweful, Katie! Considering the previous post, this latest has been more devastating for you I believe, because it feels like the one who wounded has the one who salted it up knowingly! But a great respect to your strength and belief! I’m sure this assumptions has shown or made you learn how to deal going forward now! Thanks for being courageous and opening yourself, you’re becoming an shoulder for others who’re in similar kind a situation! Huge respect to you Katie!

    1. avatar

      Yeah, the second time around was definitely more heartbreaking because it left me feeling used and a little naive for believing things were different.

      1. avatar

        I feel how heartbreaking it was! But you’re not naive, have faith in yourself! I know I can’t do much here, but all I can say is it’s time where you should know your value by your own perspective and not from others’!

        1. avatar

          Very true and a great point!

  12. avatar

    That is so rough.. Thankfully I havent done that but I did go back to an ex and we dated a second time only to break up again for the same reasons but I got to do the breaking up. I’m sorry you went through something so hard ?

    1. avatar

      Yeah, going back to an ex normally doesn’t work out well for people, but at least you got to do the dumping the second time around!

  13. avatar

    Oh unfortunately I think we’ve all been in a similar headspace where we hold on hoping things will turn out the way we want them to but they never really do. Sometimes I think, did they hurt me, or did I hurt myself with my expectations? Probably both are true.

    I’ve only had sex with an ex once, and although at the time it felt like it was a big moment for us, we clearly perceived it very differently and I did feel guilty after.

    1. avatar

      Yes, I had some guilt afterwards, but mostly just more anxiety, confusion, and ultimately disappointment. Thanks for reading!

  14. avatar

    Ugh, I know exactly what it feels like to fall into this trap! I’m so glad I don’t have to worry about dating anymore, it can be so hard on your mental health! Thanks for sharing this story and being so vulnerable. I’m glad you realized how toxic that situation was, you deserve so much better. ? Keep up the great writing!

    1. avatar

      Definitely a toxic situation! I’m glad you enjoyed reading about it, though.

  15. avatar

    I cannot tell you how many times I’ve had sex with an ex and regretted it. I will definitely not do that again.

    1. avatar

      It never seems to end well, does it?

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About Author

30ish Lifestyle blogger, relationship "expert," and modern-day agony aunt.
Sometimes humorous, always honest.