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Kevin’s Whirlwind Weekend: How One Man Tried to Save His Relationship With a 48-Hour Trip to Spain

Ever had someone break up with you because you “haven’t traveled enough”? Most of us would take that as a cue to get out more, maybe check out a new coffee shop, or plan a summer road trip. But not Kevin. Kevin’s solution? Book a last-minute, ten-hour flight to Spain for the weekend and hope his passport stamps could mend a broken heart.

This is not a travel hacking story. This is the saga of Kevin—an employee inherited by a Redditor’s wife—who took “spontaneity” to new heights, all in the name of love lost and, well, questionable logic. Buckle up, because this is a ride you won’t want to miss.

The Origin Story: Who Is Kevin?

First, let’s set the stage. Kevin was not hand-picked for his job; he was, as the Reddit post says, “inherited.” That’s HR-speak for “the last manager stuck me with this guy.” He was the kind of coworker who makes you wonder if you’re starring in a sitcom and no one told you.

Kevin’s love life, like his employment, seemed a bit… complicated. He’d been engaged, until suddenly he wasn’t. His girlfriend, finally “over him,” broke things off. The reason? Among many, she cited his lack of worldliness—specifically, his absence of international travel. Ouch.

The Plan: Operation Impress The Ex

Most of us, after a breakup, binge Netflix, eat ice cream, and maybe text our friends for emotional support. Kevin’s approach was a bit more… ambitious. A few weeks post-breakup, he asks his boss (the Redditor’s wife) if he can leave work early on a Friday. She agrees. No big deal, right? Wrong.

Come Monday, Kevin drags himself into the office, clearly exhausted. When asked what happened, he nonchalantly reveals: he’d flown from the U.S. West Coast to Spain on Friday night, spent the weekend there, and returned Sunday. For those keeping score, that’s about 20 hours of flying for maybe 30 hours on the ground, jetlag included.

The Logic: If You’ve Got a Passport, Does That Make You Worldly?

Why, you ask? Because his ex said he hadn’t traveled, and Kevin wanted to prove her wrong—retroactively. Apparently, if you rack up enough frequent flyer miles in a single weekend, you can erase years of wanderlust neglect.

It’s endearing, in a “bless his heart” kind of way. There’s a certain earnestness to Kevin’s logic: “If travel is what she wanted, I’ll travel—hard.” But, like using superglue on a shattered vase, the fix is more comical than effective.

The Aftermath: Did It Work?

Was his ex impressed? Did she come running back, swept off her feet by the scent of Madrid and the sound of castanets? We may never know. What we do know: Kevin was exhausted, his coworkers were baffled, and his boss had a new office legend to share.

On Reddit, the story has become a minor classic, collecting upvotes and bemused comments. Some marvel at Kevin’s tenacity; others gently roast his logic. All agree: it’s a tale for the ages.

Lessons Learned (Or Not)

Let’s be honest: we’ve all made questionable post-breakup decisions. Kevin’s story is a reminder that our attempts to win someone back can sometimes say more about us than about them. Sometimes, the grand gesture isn’t what’s needed—just some self-reflection and maybe a little more time spent on self-improvement (or a good nap).

But let’s give credit where it’s due: Kevin didn’t just sulk at home; he went out and experienced something new—even if it was in a sleep-deprived haze. And in the end, that’s not the worst way to start a new chapter.

What Would You Do?

Have you ever made a wild gesture to win someone back—or just to prove a point? Would you hop on a transatlantic flight for love (or pride)? Share your stories in the comments! And if you’ve got a Kevin in your life, give them a (gentle) high five from us.

After all, sometimes the best stories come from the most questionable decisions. Safe travels, Kevins of the world.


What’s your favorite office legend? Drop your own wild workplace tales below, and let’s keep the spirit of spontaneous adventure (and minor chaos) alive!


Original Reddit Post: Kevin Goes to Europe