Whether at a Michelin-starred restaurant or lounging in underwear on my couch, I love asking my dates about their exes. Some may not feel immediately comfortable diving into details about their former flings, but I find it intriguing, enlightening, and, sometimes, even hot.
When I’m on a date, I let the vibe and chemistry guide the conversation. But the more interested I am in someone, the more I want to dig deeper. It can feel awkward to ask someone if they’re emotionally available or vanilla in bed. But when I frame it through their past relationships – like asking if they’ve been in a serious relationship or dated someone with a surprising kink – they open up more easily without feeling the need to filter themselves.
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Blaine Anderson is a dating coach and the CEO and founder of Dating By Blaine.
Not every person I go out with is eager to talk about their exes on a date, though. In fact, some tend to act like I set a mousetrap on their tongue no matter what I ask. According to dating coach Blaine Anderson, this is to be expected since talking about exes is generally frowned upon – especially since it might be perceived as a red flag.
But even hearing about why a date’s past relationships ended has helped me get a better read on which people I might be compatible with and which people I wouldn’t be. Plus, I don’t consider it a total deal breaker if a date still has feelings for an ex or even if they hate them. I care more about how they talk about their ex and what they say.
One time, I realized I fit too neatly into someone’s “type,” which made me feel more like a clone of their exes than a catch. Another time, I found out one of my dates was still living with their ex . . . in a one-bedroom apartment. Another time, I discovered the person I was sleeping with was actually married with kids because I asked him if he gave his ex massages like he did for me.
The more interested I am in someone, the more I want to dig deeper.
All that to say, no matter what I find out, it’s often worth the awkwardness. Certain clues about a romantic interest’s dating history proves to be valuable and relevant to the present, whether I liked the information I received or not.
That said, as fun as hearing about exes is on dates, Anderson says it’s probably not a great first-date question. “As a blanket rule, I’d probably recommend skipping the ex stories until you’re exclusive with someone,” she says. If you want to be like me though, I don’t feel like there needs to be a timeline.
Sure, everyone has different triggers and conversations they want to avoid on dates, but someone’s romantic past shouldn’t be one of them. In an era that celebrates everything from open relationships to abstinence and living-apart-together relationships, isn’t it time we treat singles like adults who can handle the truth?
If you ask me, the best way to master the manual to someone’s pleasures, icks, and life values is through the playbooks of past players.
Jamie Valentino is a Colombian-born freelance journalist and romance columnist published in the Chicago Tribune, the Houston Chronicle, Men’s Journal, Reader’s Digest UK, Vice, and more. Jamie has worked as a travel correspondent, covering the 2022 World Cup from Argentina, siesta culture in Barcelona, and the underground nightlife scene in Milan.
