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I forgot about our crazy one night stand – until I got engaged to her brother

Published June 7, 2026 · Updated June 7, 2026 · By William Taylor

I forgot about our crazy one-night stand – until I got engaged to her brother

I forgot about our crazy one night - When I first met my now-fiancé, he was just another familiar face from my childhood – a childhood friend I’d known since school. We connected years later, and what began as a slow-burn relationship quickly turned into a whirlwind romance. After a few months of intense dating, we decided to tie the knot this Christmas. But now, as I prepare for the big day, I’m haunted by a past I’d long since buried.

A Weekend of Wild Excess

Five years ago, I embarked on a trip to Spain with my future sister-in-law, a decision that would later shape my life in unexpected ways. We spent the week partying nonstop, drinking late into the night, and sharing more than just laughs with the locals. One evening, we stumbled into an impromptu orgy, a chaotic moment that left me both exhilarated and mortified. Though I’d never considered myself a risqué person, that night was the only time I’ve ever had a lesbian encounter – a fact I’ve kept hidden from all but a select few.

It’s easy to forget the chaos of youth, especially when you’re far from home. My friend and I were the kind of people who thrived on spontaneity, and Spain became our playground. We laughed about the incident the next day, promising to keep it a secret. At the time, it felt like a harmless fling, a story to be shared with a wink and a smile. But now, with the engagement ring on my finger, the memory feels like a betrayal.

The Weight of Secret

She’s married to an older man with two kids, living a conventional life that couldn’t be more different from the one we lived in those days. She even arranges the flowers at their local church – a detail that makes me cringe. If she ever decided to spill the beans, I fear the consequences. Her brother, my fiancé, might see the entire story as a scandal, and I’m not sure I’m ready to face that.

People often assume that past mistakes fade with time, but for me, they’ve lingered like a shadow. I’ve always considered myself a stable, reliable person, yet that week of recklessness feels like a glimpse into a different version of myself. It’s hard to reconcile the girl I was with the woman I’ve become, and now I’m questioning whether I should confess to my fiancé or keep the secret safe.

Laura’s Advice: Embrace the Past

“Most of us have done things we’d rather forget, especially under the influence of alcohol. What you did as a school-leaver is ancient history and hurt no-one. It really wasn’t ‘terrible behaviour’,”

As someone who’s spent three decades in the newspaper industry, I’ve seen countless stories of people struggling with their pasts. Laura Collins, the author of this piece, suggests that our fears might be overblown. She argues that the actions taken during that chaotic holiday were a natural part of growing up, not a sign of character flaws. “You let your hair down on holiday, which is exactly what a lot of people do – although admittedly, not always in such an extreme way!”

But the emotional weight of the secret is real. Laura acknowledges the embarrassment, yet urges us to see it as a shared experience. “Why would she want to blab about something she probably winces at, as much as you?” she asks. It’s possible that my friend, now a married woman with a family, would rather keep the memory private. After all, what’s the point of bringing up a past that no longer defines her?

Still, the fear remains. If I tell my fiancé, I might be opening the door to judgment. But if I don’t, I’m living with the guilt of keeping a truth that could one day unravel our relationship. Laura encourages readers to consider how their partner might react. “Whether he thinks it’s funny, shameful or irrelevant is something for you to judge,” she writes. The key is to communicate clearly, reassuring him that your past is behind you and that your commitment to the future is unwavering.

What’s the Right Move?

Should I confess? The answer depends on how the story might unfold. Laura reminds us that everyone has a history, and over-sharing can sometimes be a mistake. “You’re under no obligation to tell him chapter and verse of your previous sex life, as he is under no obligation to you,” she notes. This isn’t about judgment, but about understanding your own motivations.

If you decide to share, make sure it’s a conversation, not a confession. Highlight your growth and how that experience has shaped you into the person you are now. But if you keep quiet, don’t forget to acknowledge your own feelings. “You know him well – how do you think he’d react?” Laura asks. The decision is yours, but it’s important to weigh the pros and cons carefully.

Before taking the plunge, talk to your friend. She’s part of the story, and her perspective might help you decide. “After all, you’d be opening up about something that involves her,” Laura says. She might have her own thoughts about how to proceed, and her opinion could provide clarity in your uncertainty.

Some secrets are best kept just that – secret. If you end up unburdening, and the relationship falters, you can always revisit the story. “If you do end up unburdening and it all goes wrong, email me again,” Laura writes. Her advice is a reminder that we’re all navigating the complexities of love and self-perception, and that it’s okay to make mistakes along the way.

For those still grappling with their own dilemmas, Laura’s column is a treasure trove of insight. From relationship advice to steamy anecdotes, her weekly newsletter offers a mix of expert tips and relatable stories. Sign up now to dive into the latest take on love, lust, and life’s little surprises.

As for me, I’m still deciding whether to tell my fiancé. But one thing is clear: the past can’t define the future. After all, the most important thing is that we’re both committed to building something real, something that deserves to be shared without hesitation.

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