Why sleeping with your ex isn't always a bad thing

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By: Arika Kim

Welcome to A Millennial's Dating Diary series, where we explore real-life interactions and the hurdles of dating in Southeast Asia. The series will feature the dating stories and misadventures of Arika – a 26-year-old, straight female marketing manager with a penchant for over drinking — and fellow millennials.

This week’s Millennial Dating Diaries is back with another controversial topic.

Before you come for me with your pitchforks and torches…

I’m completely aware that not everyone is friends with their exes, and if your ex was toxic or affecting your mental health, do not touch that person ever again — even with a sanitised 10-foot pole.

Almost three years ago, my ex *Drew, 26, and I broke up. We met in our teens in school, and for almost 10 years, I thought Drew was the one I would end up marrying.

Life inevitably threw a wrench in the system, and Drew and I ended our relationship — albeit messily.

Despite that, we were eventually able to find some closure and better our newly formed friendship in recent months. Since reconnecting, we’ve been texting almost every day, and it felt just like old times.

It wasn’t long before we started sleeping together. And frankly, it was great.

Sex with Drew felt really natural, and unlike the men I’ve met through dating apps, Drew and I have already established an emotional connection that runs deep. Plus, we were best friends before we dated in the past, so it’s not like we stopped caring for each other. In recent months, Drew has been showing up for me the way a boyfriend would, without expecting much in return.

(PHOTO: Getty Images)
(PHOTO: Getty Images)

I’m acutely aware of how rare a relationship like this. But I’m more aware of the possible pain this relationship might inflict.

When I told some of my closest friends that Drew, and I started seeing each other again (and I mean this in the loosest of terms), they reacted the way I’d predicted.

“Wouldn’t it hurt you?”, “Are you two just friends with benefits?”, “Are you guys back together?”, were just some of the questions I got.

At this point, I decided to get real with my feelings and spoke to Drew about my intentions. We opened up to each other and began answering some complex but important questions. And here’s another benefit of being involved with your ex: years of being together have made it easy for us to be vulnerable with each other sans judgement.

Here are some questions we asked ourselves:

Did we want a long-term relationship again? Not really, no.

Do we still love each other? Yes, but that’s also different.

Do we care about each other? I mean, duh.

(PHOTO: Getty Images)
(PHOTO: Getty Images)

Would we be fine with the other person dating someone else? No, but... if we’re not exclusive, we have no hold over each other.

We were also really honest and talked about our motivations, boundaries, and the importance of open communication. Sex with an ex will always be complicated, and with feelings involved, it’s always important to be honest about your motivations.

Are you sleeping with your ex because you’re lonely and they’re the most familiar person to you? Are you hoping sleeping with them would make them want you? Or are you just doing this to get some validation that you’re still a hot commodity?

Whatever you choose — and I’m in no position to judge — one thing you ought to be doing is figure out what your intentions are and whether sleeping with your ex even is something worth doing or would doing so lead to more pain.

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