True Romance: Boss Makes Indecent Threesome Proposal, Mistress Attacks Wife On Camera & Rich Men In The DMs
A married boss asks a single woman that works for him to join him and his wife in bed
It's Thursday, and I don’t know about you, but I'm ready for a little True Romance before the NFL season kickoffs tonight. I can’t think of a better way to channel the extra excitement than with talk of threesomes, mistresses and rich men in the DMs.
But before we dive into all that, I'm sure you've heard the latest news involving one of the most eligible women in Hollywood. Of course, you have.
Sydney Sweeney can't do anything without people noticing. She can't wear jeans or pretend to be a ballerina, so she certainly can't enjoy a quiet vacation with a slightly older record executive.

The casual romance, as it's being described, with 44-year-old Scooter Braun had the two enjoying Labor Day Weekend at Lake Tahoe, according to reports. Can we please let the 27-year-olf have some fun with a "very attentive" record executive?
Is that too much to ask? I don’t think so.
It's about time Sydney was back out there rubbing shoulders with older men with whom she appears to be well out of their league, isn’t it? She called off her wedding months ago. Let her have some fun.
Speaking of having some fun, is it too much for a boss to ask an employee of his if she would sleep with him and his wife? Yes, he's going to pay her for her time. Let's get into that, but before we do, go follow True Romance on Twitter and Facebook.
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The boss' indecent threesome proposal
What do you do when your boss has been obsessed with you for years and is constantly asking you to "go away on dirty weekends" because he wants to have a "filthy affair" with you? If you say quit your job or run to HR, you're way off base.
You stay, obviously, because one, you love what you do for a living and two, maybe one day you'll entertain that filthy affair and ask for some advice on how to proceed should an indecent proposal come your way.
If your instinct is to quit or rat your boss out, you need to do some serious recalibrating. Where's your sense of adventure? There's an opportunity for who knows what here. This could go in several directions.
Let's hear what this woman has to say about the situation and her boss' latest plan. She told the Daily Star, "His latest plans involves him paying me to have a threesome with his wife. I’ve met her, she’s nice."

A woman's boss makes her an indecent proposal to have a threesome with him and his wife. (Image Credit: Getty)
There are a couple of bonus points to put into the pro column. You've met her and she's nice. Let's be honest, you also don’t seem to hate the attention you get from the boss either.
"He says their sex life is flagging and having me in the bedroom would perk things up," she continued. "Apparently, they’ve done this sort of thing with other women in the past and it’s worked a treat."
This sounds more like a win-win the more she keeps going. But that's probably why she's sharing this in the first place. She wants someone to talk her out of it.
"The problem is that he has me over a barrel," she explains. "He knows I’m single and saving for a place of my own. He knows what I earn and won’t give me a pay rise. He describes his offer as a ‘lifeline’. Is it?"
A lifeline? Is he nuts? This is way more than that. I'd say he's as bent over the barrel here as she is, which is an interesting thing to say while laying this all out.
You're going to quit one day eventually anyway. Why not do so after creating a romantic memory first?
This Week in True Romance:
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Ring doorbell footage shows married man’s mistress attacking his wife
Let's head down to Florida where a married man's mistress was allegedly caught on a Ring doorbell camera attacking his wife. It's not the ideal welcome home after spending the evening at Universal Studios with your kids.
39-year-old Melissa Mansingh showed up to her boyfriend's home late on Saturday, August 23, according to an arrest report from the Lake County Sheriff’s Office, after the boyfriend spent the evening at the amusement park with his wife and two kids.
She reportedly rang the doorbell repeatedly and the wife answered it. Now here’s where the husband/boyfriend could have stepped in and made it clear that there was no need for fighting. They could all find a way to get along.

A man's girlfriend was caught on a Ring doorbell attacking his wife at their home. (Image Credit: Getty)
He didn’t do that. Instead, his girlfriend allegedly forced her way inside and attacked the wife by pulling her hair, kicking and hitting her. The report from the police says that this is when the husband decided to step in and separate the two.
Clearly too late. The mood was ruined at this point and any chance for love, not war, was long gone. He escorted his girlfriend outside while his wife called the police. They arrived shortly before 11:30 pm.
That's what you call a ruined rest of the weekend right there. The girlfriend had a different version of events for officers. One where she arrived at the home to pick her boyfriend up, walked into an open front door, and was attacked by the wife.
The Ring doorbell footage told a different story and so did the scratches on the wife's face. Mansingh was arrested on burglary with assault or battery charges. She was taken to the Lake County Jail and released after posting her $10,000 bond.
I might just be a softy deep down, but I have a gut feeling that these three are going to work this all out. It probably won't be today or even next week, but they're going to realize it's better to love than it is to fight. That's my hope anyway. Good luck to them.
Flown out by rich men who slid into the DMs
Before we wrap up for the week, we're going to take a look at a few stories of love in the DMs. Specifically love in the DMs from wealthy men who slide in and fly out.
Someone took to Reddit to ask the "Ladies who’ve been ‘flown out’ to vacation with a wealthy person who slid into your DMs. What experiences have you had?"
There's a wide range of wealthy men making those slides into the DMs from an MLB player to a YouTuber, and even an OnlyFans subscriber.
And you better bet your ass someone found love in the DMs. Who knew there was so much fun to be had? This is what could happen when you check those direct messages.
- I had a sugar daddy who flew me out to New York. However, he ended up breaking up with me before the trip actually happened, because he was struggling too much with jealousy about me having other partners, despite the fact that we were both polyamorous and both knew about each other’s other partners before the arrangement started. I went on the trip anyway, since it was already booked, and ended up meeting my now-wife on that trip.
- I'd never acknowledge a guy in dm's but years ago in my 20s I did a potentially stupid thing. I was talking to a guy on a dating site. We hit it off and started talking and texting. He flew me out to his city and put me up in a really nice hotel and spent the weekend showing me around and taking me out to nice restaurants. We became friends and remained friends for many years but neither of us wanted to move to the other city but he was a great guy that treated me really well and was always very respectful. I hope he found his perfect woman.
- I’ve been flown out by someone I met at a music festival. Long story short, we spent valentines together and then the next day he implied he had a gf, so we’d have to be a secret. So, that was the last time we spoke. Oh the expectation was sex but I was young and dumb and didn’t realize that at the time.
- Met someone at a friends wedding and we hooked up. Followed on IG and he flew me out to NYC for my birthday and we saw broadway, a concert of a band he like, and had dinner with our mutual friends. However he was sober for like 10 min of the whole thing it was crazy. Since we hooked up the first night we met he sort of expected it this trip which only happened partially because he was so drunk the first night, and then the second night he was going to keep going out for drugs so I went back to the hotel at like 230am lol. It was the only thing of the sort I’ve ever done and now it’s a wild story I can tell
- Last year, my best friend and I were flown to Cancun by one of my top 5 fans in OnlyFans. Meeting through OnlYFans is NOT allowed, but obviously you jump into any other chat as soon as you see a guy's serious. Anyway! The guy was swinger (and so are we) and he wanted to invite us to a swinger resort in Mexico (Temptations). Both my best friend and I were allowed to bring someone else, but those had to pay for their tickets. Our tickets, and 70% of the hotel expenses (more or less) were paid for. We paid for some activities and a couple of tours and trips. The experience was... Underwhelming.
- I have a handful of times. The most recent one was an MLB player I met on Raya. We had already gone on two dates when he was in my city, then he flew me across the country to his home. Met some of his friends and had a decent time, but he was a little weird (has a bad reputation for being an egomaniac) and it never really turned into anything. I slept in a separate bedroom with a separate bathroom, my request which he (and any decent man) would happily oblige. Money wasn’t a part of it, he paid for the first class flights, car service, food, and my dog’s boarding but didn’t take me shopping or anything.
- I followed a YouTuber on Instagram. He wasn't really my type, but I enjoyed his content. He followed back. Then we started reacting to each other's IG stories. Completely harmless. This went on for five years or so. One day we were texting more than usual and he suggested we should meet in London as he has work related things to do in the UK. For context: He lives in the States while I'm from a European country. So he booked me a flight and even my own hotel room. I didn't really need my own room though. It was a lovely weekend, but nothing more than that. We tried to meet again multiple times, but it just didn't work out. We still follow each other and even react to each other's social media content - but that's it. I'm in a very happy relationship now and he even likes the pictures of me with my boyfriend :)
- He’s not "wealthy" but has way more money than me when we met. I also did the sliding into DMs but not like how the phrase usually means when you slide into somebody’s DM lol. Anyway he flew me to Thailand and so did he after talking on Instagram for 3 months. We got engaged on day 4 of a 7 day trip and uhm we’ve been married for 5 years 6 months now
- I had a guy fly me out to Amsterdam (I'm American) after my divorce and he was great except he couldn't perform sexually and I wish I had known that before I hauled my cookies 5000 miles.
- Guy followed me on IG. Was cute so I followed back. Messaged one another a few times and then he asked if I wanted to video chat. I was at home with time to kill and I agreed. He said he just wanted to see I was a real person because he was going on a diving trip to Cabo and would fly me out for a few days if I was interested. Stayed in a gorgeous penthouse suite with an amazing view, ate at good restaurants. He was very attractive just not very tall.
True Romance
- Phil S writes:
Hey Sean. Not sure if this will fit into anything upcoming you have but feel free to keep it on the back burner for the future. Somehow unbeknownst to me, I have found myself dating married women multiple times, yes I was the other man. It’s like some strange superpower to attract other people’s wives. I don’t know what it is, how it happens, or why the husbands always find out about me and just tuck their tails and submit to what’s happening. I developed a good personality and great sense of humor, so I’m not overly attractive or anything. I also do not pursue married women, thats no kink of mine. Every time it’s happened she threw herself at me, once literally. However I will say there is an excitement factor to it that is unmatched. The fear at the beginning of being found out, to being discovered and basically telling him "Hey you did this to yourself. You did something that lead her away from you and to me, so I’m gonna keep doing what I’m doing." It’s fun, but it comes with a short fuse that burns out a few months after he finds out and they still live together. I really don’t want to ruin any marriages or steal any other man’s wife, and I’ve told myself I’ve learned my lesson each time…. but history tends to repeat itself.
I believe I read that it’s your birthday. Happy birthday! If not, uh happy upcoming birthday sometime within the next 365 days. Keep up the great work, I love reading your stuff.
SeanJo
Hey Phil, thanks for sending this in, and thanks for the birthday wishes. Some guys have all the fun. Not that you ask for it, but you have to admit that it was never boring when these married ladies fell into your lap. Best of luck avoiding the married ladies out there.
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That's all this week. I don’t have a poll ready to go. Let's pick that up next week. The results of last week's poll, which was "Have you had a relationship with an ex's relative?," revealed you're a boring crowd. 90.5% said No.
Send your own stories of romance, anonymously if you prefer. We'll do it all again next Thursday. The inbox is always open - sean.joseph@outkick.com. And don't forget to follow along on Twitter and on Facebook.