I thought turbulence would be the worst part of flying. Turns out, nothing shakes you harder than seeing your ex sugar daddy on the same plane… especially when you’re traveling with the new one.
Let me back up.
For two years, I was with someone I used to call my “sugar boyfriend.” He was kind, generous, attentive—the kind of man who didn’t just spoil you, but made you feel safe. Think: surprise Dior, perfectly chilled rosé, and long conversations about life at 2 a.m. But like many stories in the sugar world, it ran its course. He wanted a real future—weddings, kids, the works. I… didn’t.
We parted ways quietly, respectfully, and I thought that was that. No drama. No lingering texts. A clean, grown-up break. Or so I thought.
The Flight Where Everything Went to Hell
Last week, I went on a little getaway with someone new. We’d only been seeing each other for a few weeks—not serious, but promising. Let’s call him New SD. He’s charming in a corporate, finance-bro kind of way. Think: Patagonia vest, slick hair, way too into his mileage status.
Anyway, New SD was handling “important business man things” in the lounge and told me to board first. So there I was, strutting down the aisle of a business class cabin with my Dior purse swinging from my shoulder and my Rimowa carry-on rolling behind me—both gifts from my ex SD. Yes, the irony was already thick in the air.
I’m halfway to my seat, head down, trying not to make eye contact with anyone, when I hear: “That’s a beautiful purse.”
I look up… and there he is. My ex SD. Sitting in 3A, legs crossed, flipping through an in-flight magazine like a scene straight out of a movie.
Suddenly, I’m in a Rom-Com. But Not the Good Kind.
He looks up, smiles—cool as ever—and stands to lift my suitcase into the overhead bin. Just like old times. I smile back, trying to keep my face from melting off. We exchange pleasantries. It’s casual. Friendly. And then he asks: “Are you going on a trip with your sister?”
And then, as if summoned by the cringe gods themselves, New SD appears behind me. “Hey, babe,” he says, placing a hand on my waist. “All good?”
My ex turns, offers his hand with a smile that’s way too charming, and says, “Hi. I’m [Ex SD’s name]. Lovely to meet you.”
And just like that, the gates of hell opened. I was the prize in an accidental sugar daddy showdown at 35,000 feet.
The Luggage That Ruined My Life
It gets worse. My ex, ever the eagle-eyed detail guy, glances up and goes, “Hey, you’ve got a Rimowa twin!”
New SD laughs politely, glances at mine, then back at his. “Oh yeah, same model.”
Yeah. Because they’re literally from the same man.
I wanted to fall through the floor, but unfortunately, Boeing hasn’t installed that feature yet.
Three Hours of Silent Torture
We all ended up seated within the same sad triangle of awkwardness. I was next to New SD. Ex SD was right in front of us. And we had three hours of pretending like this wasn’t the most excruciating moment of my adult life.
There was no real drama. No confrontation. Just… tension. Thick, uncomfortable, “am I sweating through my blouse” kind of tension. My ex was perfectly pleasant, of course. He asked New SD how he liked his watch (a Rolex I had once complimented). He complimented the airline’s champagne selection (which we used to toast with). He even chuckled when the flight attendant offered warm nuts.
Me? I sat there, clutching my Dior like it was a flotation device.
The Emotional Aftermath
I’m not going to lie—seeing him again, hearing his voice, being reminded of all those tiny habits and inside jokes—it hit me harder than I expected. Maybe I wasn’t as over it as I thought. Or maybe it was just the humiliation of it all, the realization that the past has a funny way of boarding the same flight as your future.
When we landed, we all went our separate ways. New Sugar Daddy never said much about the encounter, but I could tell he was… curious. Maybe suspicious. Maybe impressed. Who knows. He hasn’t brought it up, and I’m not volunteering it.
What I Learned
1. Always check the passenger manifest before flying. Kidding. (Kind of.)
2. Don’t travel with gear gifted by your ex—especially if there’s a chance he might appear in the first-class cabin like a ghost in Gucci loafers.
3. Closure doesn’t always come in candlelit conversations. Sometimes it comes with a boarding pass and a side of emotional whiplash.
I survived. Barely. And now I have one hell of a story to tell.
Next time I travel? I’m packing a neutral tote. And maybe an alias.