True Romance: Man Wants Hall Pass Trips To End After Baby, Man Slept With Wife's BF & A Reader's Close Call
Welcome to the latest edition of True Romance with SeanJo.
This week we're going to learn about something called hall pass trips. A couple of habitual cheaters implemented it as a way not to cheat on one another.
The couple has now had a child together and one of them is ready to put the hall pass trips in the rearview mirror. That sounds reasonable, but not to the new dad's partner. She wants to keep the fun going.
From there, we get into a messy situation where a married man is feeling guilty after he slept with his wife's best friend while they were separated.
To bring things home this week is a reader submission where a friend of a married couple asked if she could watch them get it on.
Send me those true romance stories - you can do so anonymously. I want to hear from you. Whether it's stories, comments, or questions, send them my way, and we'll unpack them.
Send the emails my way at sean.joseph@outkick.com.
Hall pass trips
I think most people know what hall passes are, but for those of you who don't, it's pretty much permission given to you by your partner to cheat. A couple that has been together for eight years now has taken this concept to a new level.
They've implemented hall pass trips. Now I don't know if the 41-year-old man and his 32-year-old girlfriend are the inventors of this or not, but it's the first time I've heard of such an arrangement.
Their relationship started as an affair. Both of them were cheating on their partners with one another and when they discussed making their relationship work they came up with the idea of asking for a hall pass when they wanted to venture out of the relationship.
A couple has scheduled hall pass trips so that they can cheat on each other for 8 years. (Image Credit: Getty)
This has worked for them for eight years. He explained how their hall pass arrangement works, "When one of us asked for a hall pass. We both booked trips, had our fun and then came back together. I’d say we did this a couple times a year on average."
He admits that the arrangement might not be the smartest idea, but it seemed to work for them. That was until last year, when his girlfriend got pregnant.
They put the hall pass trips on hold during this time and now that their son has arrived and is 4 months old, his girlfriend is looking to get the fun going again by resuming their hall pass trips. He's not too sure now that there is a child involved that it's going to work as well as it did.
"Last night my partner discussed getting back into the groove and having a hall pass trip and how we would manage that now that we have a kid. We obviously can’t do them at the same time so she suggested we do them separately," he said.
"Now, I know sitting at home with a baby while my partner is getting railed for a whole weekend will not work for me and I know her, it won’t work for her either. I straight up asked her how a Saturday would go when she knows I’m getting laid while she is rocking a baby. She said it would be tough, but it’s worth it for what we gain."
He suggested the possibility of trying some other form of mutual agreed upon cheating, but she's not going for it. The hall passes have worked for 8 years now and a child isn't about to ruin that.
"I loved the hall pass trips, but I feel like this is a recipe for disaster that will make us both grow resentful," he admitted. "No idea what to do, but just wanted to vent before I have another crack at this argument."
I don't know about you, but having a child without figuring this out ahead of time gives me a lot of hope. A different couple could run into problems, but these two are innovators. They want one thing in this world more than anything else - they want to cheat.
They've made it work for almost a decade now with their hall pass trips and with their backs against the wall they'll figure this out. One way or another, they'll be hooking up with others and doing so very soon.
Slept with my wife’s best friend
Now to a one-night stand that has a married man in a tough spot. Does he tell his wife about sleeping with her best friend while they were separated or keep it to himself?
Let's see what he has to say about the situation.
"This occurred once. Also happened when my wife and I were separated. Coincidentally, her best friend was also going through a separation; although they decided to get a divorce," the man says.
"My wife and I decided to remain married. I can’t help but think that maybe she shouldn’t know. What good will that do? We’ve worked so hard to make it work, and I want it to be worthwhile."
A married man slept with his wife's best friend while they were separated. (Image Credit: Getty)
He's put himself in a really tough spot here. He wants to have his cake and eat it too. He slept with his wife's best friend and now he's back with his wife and doesn't want to ruin it.
"I’d like to know what to do about this. I can’t stress enough how much I regret doing what I did," he added as he wrapped his search for advice up. "This was at a time where my marriage was at an all time low."
There's a good chance this blows up in his face whether he tells his wife about it or not. Whether it's in a week from now, a year, five years or ten, his wife is probably going to eventually learn about his one night with her best friend.
I know this seems contrary to my romantic nature here, but he has to go out for milk and never return. He has to start a new life elsewhere, potentially a foreign country.
In a way, it's the ultimate in romance.
He loves his wife so much that he doesn't want her to go through the heartache of finding out that her best friend is willing to take advantage of her husband at his most vulnerable.
Love found in the dumpster
Did trash bring this next couple together or did navigating life, even in a dumpster, with an open heart do so? That's what I'm going with.
Who knew there were such treasures as the bottom of a dumpster? David Sheffeild and his wife Erin did, that's who.
According to the NY Post, the two met during David's college days at the bottom of a dumpster in Buffalo and have been together for 15 years now.
A man and woman found love in the bottom of a dumpster. (Image Credit: Getty)
"We met in a dumpster. I saw him, popped my head over and asked what he was doing," Erin said. "He jumped out, we cleaned up and spent the day dumpster diving."
The two exchanged numbers and started hanging out.
They eventually became more than friends and then, in 2021, the dumpster diving couple got married. The couple then got pregnant in 2023 and loaded up on baby supplies found in dumpsters.
Good luck keeping that kid out of the trash. This is a family built off of love found in a dumpster and that's a family that's going to keep passing down this skill.
There's more than trash in dumpsters after all. There's love and as much as $20,000 in treasures they're able to pull out every year.
I can't help but think about the couple who tossed their love into the dumpster for these two to find. What happened to them? Were they eventually able to find love for themselves? I hope so.
Third Wheel in a happy marriage
Now to a reader submission that puts a happily married couple in a bizarre situation. A friend of the couple asked them if she could watch them get it on. Let's see how this plays out.
- Anonymous writes:
Sean Jo,
Great stuff as always, I appreciate your craft. Today’s TRUE ROMANCE about the wife’s friend throwing a line for a threesome struck a chord with me.
I’m 60 years old and faithfully/happily married for 37 years. Back when my wife and I were in our 30’s a mutual female friend (someone I have known since kindergarten and my wife was friends with since elementary school and was in our wedding party) made a direct request to watch us "do it".
The friend was in another of her endlessly poor and abusive relationships, this time her husband and the father of her two children. From a purely physical perspective, she is still a 10/10, thin waisted, thin and athletic, with a couple of surgically enhanced points "sitting way up firm and high" (Bob Seger Night Moves reference).
I digress. My first thought was "what could it hurt, she’s just gonna watch". Full disclosure my wife and I are not nudists or exhibitionists. My nearly immediate second thought was, there’s a reason I liked this woman since kindergarten but never chased her. She was always "the hot chick" but her personality was abrasive, entitled, obnoxious, demanding, and she was constantly creating drama.
The thought of THAT mental train wreck getting between the woman I love and three minutes (let’s face it I’m being generous) of basic gratification was enough to douse any flames of passion blinding me. My wife was a NO right out of the gate. The subject never came up again, and a year later I was promoted and relocated the family hundreds of miles away and we haven’t seen her since 1999.
------------
What a way to end the week. It sounds like a disaster was avoided here, and the real story of romance is the 37 years of marriage. Not even a 10 out of 10 could put that at risk all those years ago.
Congratulations and well done on dodging the close call with an abrasive, drama-filled smokeshow.
I'll see everyone next Thursday. In the meantime, send over your stories of true romance, your comments, or your questions to sean.joseph@outkick.com.