True Romance: Woman Joins The Mile High Club With A Stranger, Divorcee Struggling With New GF's Past & More!
What better way to pick up where True Romance finished off last month than with a chance meeting on a plane turning into joining the mile high club with a stranger? I can’t think of any.
These two had chemistry and didn’t know if they would ever cross paths again. So they went for it and now have a unique story to pass down to the grandkids one day.
There's no need to exchange numbers and make things awkward. They're in an exclusive club now, and they'll always have that. No pretending like they might want anything more.

When you think about it, that's the beauty of passion and romance. You don’t have to make it any more complicated if you don’t want to. High-fives all around for these two.
Now, of course, we're not going to pretend as if every relationship is a smooth one. Or that everyone is as mature as these two members of the mile high club we're going to discuss.
That's not reality. Sometimes you struggle with a new girlfriend who had a sugar daddy when you started dating and has a past that includes sleeping with her bosses.
That or your girlfriend proves she's crazy after you get caught cheating on her. Digging into those on Thursdays is how we balance out the nearly perfect mile high club story.
Life is complicated and nobody's story is perfect. We make mistakes and we learn from them.
Woman joins the Mile High Club with a Stranger
Let's start the week with a decision that I'm sure both involved will never regret. They were on an overnight flight from Los Angeles to London and made the long, boring flight one to remember.
The 24-year-old woman says she was seated next to a man she guessed was in his late 20s and who she described as "annoyingly attractive - tall, scruffy beard, dark eyes."
The two didn’t talk very much during the first part of the flight. That changed a few hours in, after they had dinner and "a few glasses of wine (thank you, in-flight service)."
The guy was annoyingly attractive and funny. The woman then said the magic word for hooking up with a stranger on an airplane. She admitted, "there was chemistry."

Woman on a long fight says she joined the mile high club with a stranger. (Image Credit: Getty)
You bet your ass there was chemistry. She shared on Reddit, "At some point, the cabin lights dimmed, and people around us were dozing off. We were still talking, but our voices got lower, leaning in closer. My hand brushed his arm, and I swear, there was this moment where we both realized oh, this is happening."
She doesn’t recall who made the first move, but eventually "He leaned in, whispered, ‘Bathroom?’" She was all in for the adventure.
"We did the whole ‘casual’ one-after-the-other thing, but let’s be real—flight attendants know when two people sneak off like that. I barely had time to process before he pulled me in, locked the door, and kissed me," she wrote.
"It was rushed, desperate, hands everywhere, the thrill of knowing we could get caught at any second making it ten times hotter. It wasn’t exactly romantic, but it was electric."
They did their best to act normal, although it was anything but a normal flight. They didn’t talk much after joining the club together. They never exchanged numbers, "just a lingering glance when we landed and went our separate ways."
See, I told you this would be one they would pass down to their grandkids one day.
Does anyone have a mile high club story that tops that? If so, I want to hear it. The inbox is open sean.joseph@outkick.com.
This Week in True Romance:
A divorcee struggles with his girlfriend's interesting past
They can't all be as easy as the mile high couple. Some are messy and this is one of them. A divorced man jumped on a dating app to get back out there and landed on his feet with a woman who eventually became his on-again, off-again girlfriend.
It wasn’t serious at all at first. He was newly back on the dating scene following a divorce and so was she after a long-term relationship with her ex-boyfriend.
They would hang out, hook up, and go to the gym together. She worked in an office nearby so, even though it wasn’t serious, they were together a lot.
During this time, he found out that she had a side gig, flirting with wealthy men. She even had a sugar daddy that he admitted on Reddit, "paid for us to go to Hawaii once (he didn’t know I was with her)."

A man is having trouble with his girlfriend's past. (Image Credit: Getty)
He didn’t mind her side business as they weren’t serious. She had told him she spent the three years she was with her last boyfriend cheating on him. She was clubbing and getting around at that time. He puts the number of guys she cheated on her ex with at 30.
There were "Plenty of one night stands," he explains. She "Slept with a couple of her married bosses several times, a high school friend, a married gym buddy, and guys at the club. Plenty of people they knew in common."
They've now hit the three-year mark in their on-and-off relationship, and he's still having a hard time getting over her past. There's the wealthy old guys, the sugar daddy, and the 30 notches on her belt during that time that he's struggling with.
I think most people know how this one’s going to end. He's asking for advice with the answer right in front of him. This is an easy one. He needs to just go ahead and marry her now.
That's how this plays out. She does the whole loyal wife thing, they have a couple of kids, then boom, she gets bored and goes on another run. Before he knows it, she's collecting child support and alimony.
How does she pull that off if she's the one cheating? Because he's not going to go anywhere, and then he's going to go out and cheat.
She will then pull the plug and, before he knows it, she's back flirting with old men and has a couple of sugar daddies piling on top of his money in her bank account.
There's not much anyone can do except sit back and grab a bag of popcorn. Best of luck to him though.
Caught cheating with three women
We're going to wrap up this week with a classic bullet-dodged story. There are things that come up in every relationship that are either dealbreakers or things you're willing to live with.
This story is one that reveals that some dealbreakers are well hidden until the very moment that they're not. The discovery of messages on a phone helped to uncover what was hidden.
A woman found out that her boyfriend had been cheating on her with three different women after finding multiple text message threads on his phone.
She couldn’t continue in the relationship after that. It was over. But she also couldn’t simply break up with him. That would be silly. She instead spent days working on a project.

A man dodges a bullet after being caught cheating by his girlfriend. (Image Credit: Getty)
It was a redecoration project involving her boyfriend's room. She said, reports the Daily Mail, "I decided to redecorate my boyfriend's room. He has been cheating with not one, not two, but three lovely ladies."
She then spent four days collecting and printing out the evidence of his misdeeds before heading to the hardware store for some glue.
That was time spent gathering what she would need to wallpaper her boyfriend's room with the text messages he had sent to other women. That took another two hours.
Talk about a bullet dodged here. Can you imagine being in a relationship with this woman? No wonder he was out getting to know other women.
I'm not saying he couldn’t have broken up with her instead of going the cheating route, but imagine how she would have responded to that news.
If it took cheating for him to put an end to things, so be it. In the long run he'll be better off.
Couple divorce because wife is a Swinger
- Jim in NC writes:
SeanJo:
The wife sounds like she had LOTS of experience in cheating on her husband.
What I don't understand is how she made a "rookie mistake" w/ smuggling the sex toy back into the house.
When having an "away game", you keep separate sex toys thst you leave at the away field. "Home toys" are for the home! 😉
SeanJo
For those who missed it, I wrote about a man discovering that his wife was cheating on him with another couple after she was caught trying to sneak a sex toy back into their home.
It was a tragic reminder of what can happen when you trust a little too much. I responded to Jim by saying that my guess was that she got too relaxed.
The husband didn’t make a big deal about a hickey on her boob one time, and she probably figured even if she got caught that she'd be able to talk her way out of it.
That wasn’t the case. His hands were tied. Divorce was the only option
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That's all I've got this week. Be sure to follow along on Twitter and feel free to send questions, comments, stories, and whatever else you like my way.
The inbox is open sean.joseph@outkick.com.