Is it normal to be embarrassed about the people you've slept with?

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.

Lately, I’ve been thinking about someone I know I shouldn’t be thinking of, and it’s not in the most romantic of ways.

Instead, I’ve been dealing with some form of regret every time I think about this person.

*Jack, 28, was someone I was romantically involved with, and these days, whenever I think of him, I cringe a little bit at how I was ever sexually attracted to him. But, to be fair, there is nothing physically wrong with Jack. On the contrary, he’s a perfectly fine human specimen. It’s just… well, me.

For those new to this dating column, here’s a bit of a back story: Jack was someone I dated for a while. In some ways, he was everything I wanted in a partner, but the sex was terrible, and I wasn’t quite able to move past that in our relationship. Personality-wise, Jack also had the tendency to be overly negative about situations, and looking back at our relationship, I realise how that impacted how I saw life.

Some days, when I think of Jack, I shiver a little thinking about how I stuck it out in our relationship for as long as I did because, looking at him now, there’s nothing about him that attracts me. In hindsight, I wonder if I was just infatuated by the idea of a relationship with someone like him.

In fact, my embarrassment around the whole situation is so bad that, once, when I saw Jack at a pedestrian crossing, I avoided crossing the street so I wouldn’t have to bump into him and make small talk.

This got me thinking if it was normal to feel embarrassed by the people you used to sleep with or been romantically involved with, and if anyone else has felt the way I did.

“To some degree, I think you’re always going to be a little embarrassed by at least one person you used to date. I know I’m embarrassed by the first boyfriend I ever had at 16!” says my friend *Kourtney, 30, who is now married with a son on the way. “When I look at some of the things he shares on Facebook and how cheesy he is with his girlfriend, I cringe thinking how that could have been me.”

“Of course! I regret not getting to know them better and finding out if our relationship requirement aligns before sleeping with them,” says my friend Sarah, 26. “Sometimes, you just get carried away, you know?” she continued.

So what is it about our past relationships, situationships, or even just one night stands that makes us all sort of embarrassed?

I decided to bring this up with my therapist, who also happens to be a relationship expert.

“I reckon you’re feeling this way because when you look back, you’re embarrassed at how you allowed yourself to put up with so much and how you’ve allowed yourself to accept less than you deserved,” she reasoned. “It could also be because you’ve realised he wasn’t actually someone you’d normally be attracted to, and yet you fell for him.”

To some degree, my therapist was right.

I felt all those things, and it’s definitely influenced how I viewed Jack once things ended between us. Even now, when I see his name appear as a viewer on my Instagram stories, I get a slight tingly feeling, and it’s not in a good way.

“I think it’s good if you tried to reframe the way you think of Jack in your mind. Instead of thinking of him as a mistake in your life, think of all the ways things have gotten better after being with him, and all the things you’ve learned from being in a relationship with him,” advised my therapist.

Truth be told, I’m still working on it. While I might take her words into perspective, I’m also learning to forgive myself for past “mistakes” in relationships, but it isn’t always easy.

*Names have been changed to protect their identity

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