True Romance: Cheating Wife Hooks Up With Boss Husband Marries Boss’ Daughter, Billboard For Love & Crazy Exes

It's been said before, and it will more than likely be said again. Nothing says True Romance like Charlie Sheen. His claim that he slept with 47,000 women is a prime example of that.

I know it seems impossible for the 60-year-old actor to have slept with that many women in his life. But let's not forget that there’s a lot that can be accomplished when you allow yourself to be chauffeured around by romance and drugs.

Plus, according to Charlie, he got started at 15 with an escort named Candy that he found in the Yellow Pages. After all these years, he still remembers his first.

As much fun as Charlie is having reliving his love stories, he's not the only one who is making headlines this week. Believe it or not, people still can’t get enough of Bill Belichick's love life.

Who would have thought during his run at the helm of the Patriots' dynasty that in 2025 we'd be talking about that? I don’t get the obsession with it, but here we are.

He's a wealthy 73-year-old man who happens to be dating a 24-year-old. Big deal, am I right? These two are clearly, to anyone with a set of functioning eyes, in love. It's a beautiful thing to see.

But for some reason, they can’t be left alone, and this week this headline from US Weekly came: "Who’s the Real Jordon Hudson? Friends and Sources Share New Details About Bill Belichick’s Girlfriend."

I don’t need to read this to know who Jordon is. All I have to do is look at the Tar Heels sideline to know that she's the love of Bill Belichick's life. 

That is what we're all searching for. It sometimes arrives in moments when we least expect it, like it did for a man who found love through his wife's affair with her boss.

He's batting lead-off this week. Before we get going, go follow True Romance on Twitter and Facebook. Now to the man who found wife number two when wife number one decided to cheat.

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My wife had an affair with her boss, then I married his daughter

This man never gave up on love. His first wife's affair with her boss led him to find his new love. That's because he didn’t shut down completely when he found out about the affair. He kept going.

The 35-year-old man is now married to a woman 11 years younger than he is. They've been married for almost a year now, and he says, "Things are great."

His ex-wife doesn’t agree. She thinks the situation is crazy, but she's the one who led him to find his younger wife.

The man met his first wife in college. They married after they graduated and had a daughter a year after that. That's when the arguing started, which he chalked up to the stresses of being parents for the first time.

A man finds love after his wife cheated with her boss. His new wife is the boss' daughter. (Image Credit: Getty)

"Looking back now I know the signs of the affair were clear but when H [who he refers to as his first wife] said she needed to work late, I really believed her. At the time she made more money than I did so I thought she was working to provide for those reasons, plus I was taking a lead with the child care stuff so that meant I was distracted from a lot of stuff other people probably would have spotted," he said, reports The Mirror.

"Sounds silly now, but I didn't mind H spending time away from me and our daughter because I thought she wanted to see to it that our child had a better start in life than either of us had come from."

His wife's boss was married to a woman who had cancer. So, despite the signs, he didn’t think it was possible for the boss to cheat on his wife with cancer. But he was about to find out that he would and it was the boss' daughter that told him.

"I'd met my now wife, who I'm going to call S here, before so when I found her waiting out our building one day when I was getting my daughter home from school I knew who she was, but the news of the affair was hard to hear," he revealed.

"I had to believe it though because S had come with pictures and screenshots of messages, some of which said very bad things about me and S's mum. Afterwards, I confronted H and she didn't even deny it, she left me that night, and by the way didn't even say anything about our child when she was walking out."

A relationship slowly developed between the man and his wife's boss' daughter. Then she invited him on a trip when she graduated from college, and they were a couple from then on out.

A year and a half after the trip, they were engaged and then eventually tied the knot. His ex-wife, who has since their divorce moved on with her boss, didn’t approve of them getting married.

"I'm told the general tag line was that it's crazy to marry a younger woman just to get back at my ex, crazy considering the age difference between H and AP is actually bigger, also after all of these years, H is saying she cares about the message I'm sending to my daughter," he added.

"That's where I'm actually having some self-doubts now, actually. I do love S, but I also love my daughter, and I've been wondering what kind of example I am sending to my daughter."

What kind of example did he set for his daughter? The kind that says even if your wife cheats on you with her boss, you don’t have to give up on love. You can pick up the pieces, marry the boss' daughter and live happily ever after.

This Week in True Romance:

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Can you find love with a billboard?

That's the question one Bay Area bachelorette is trying to figure out. Lisa Catalano has had too many bad dates and decided that putting up a billboard would be a good way to find "Mr. Right."

The billboard has a picture of her on it with her website marrylisa.com. That's where you can apply to be her future husband. And people say dating apps are romantic.

"I just want to meet somebody," Catalano said. "And I was just not having any luck any other way."

Why not toss up a billboard? If you can’t find love that way, where's the hope for others in similar situations?

A woman is looking for "Mr. Right" with a giant billboard for men to apply to be her husband. (Image Credit: Getty)

"You know, it just comes down to chemistry. But, you know, it’s things like religion, politics, lifestyle. I want somebody who leads a healthy lifestyle like I do,"Catalano added.

"And somebody who wants to get married and have kids. Because that’s something that’s really important to me."

The billboard has been up for the entire month of September and, surprisingly, she's had to put safety measures in place after one of her TikTok posts went viral.

And going viral was the last thing she wanted. She's not in it for internet fame.

"I’m real. I’m not [looking for fame]," she said. "I guess that was something that came up, too. I’m definitely a real person. This is a real endeavor, and my primary goal is to meet the love of my life, to get married and to try to start a family."

Catalano has loved and lost before. She was engaged before her fiancé died in late 2023 from a terminal illness. Now she's ready to love again.

She's still going through the applications with hopes that her future husband is among those who have applied. How can you not root for her? You'e crazy if you think she's not going to find her soulmate with a billboard.

What are your crazy ex-girlfriend/boyfriend stories?

This one's self-explanatory and the Redditors ran with it when it was posted on the site. Some of these crazy exes went too far, like the one who liked Nickelback and the other one who couldn’t handle a simple Sports Illustrated Swimsuit magazine.

• Ex girlfriend tried to hit me with her car. Chased me down an alley in which a fence too high to jump was on one side and condos on the other. Proceeded to call me next day at work and tell me that I looked like a sexy cheetah running away from her car.
• My girlfriend told me the week before I went to college that I got her pregnant knowing that we were not going to date long distance. She sent me a picture of a stock photo pregnancy test she cropped that was positive I literally just Google searched "Positive Pregnancy Tests" and it was one of the first ones. I made her come over and take another one. It was negative, she left.
• My ex found out my rebound had pierced nipples. Completely normal response: She pierces hers, shows up at my apartment, climbs up to my balcony and waits for me to come home, topless. Not weird at all.
• One of my exes was convinced that I was cheating on her with both my mother and sister, so whenever I spent time alone with either of them I was bombarded with text messages and phone calls. When my mother, sister, and I went on a family vacation to New York City, she was insistent that I sleep in the hotel's fire escape because she thought I was going to have sex with them.
• My ex somehow thought that taking her to a fancy dinner meant that I was going to propose to her. When it didn't happen, it lead to a downward spiral… She also once pretended to faint during an argument. It was super awkward.
• He ended up in the in dryer at my apartment complex in the middle of the night naked and crying. Yes, you read that correctly and no, I am not making this up (I wish I was).
• My first girlfriend tried to convince me that she was a 300-year old succubus in the middle of a make-out session. I thought she was just joking, trying to make it a little more kinky or whatever. we kept going, and then went our separate ways.
• I had a crazy ex girlfriend who kicked me out of a car and made me walk home bc I said I hated Ke$ha
• So, I dated this guy for about two months. I wasn't really into it, so I broke up with him. About a month later, I start getting these insane texts and hang-up phone calls from an unknown number. It turns out he was engaged, and I had been the "other woman," unbeknownst to me. The person texting me was his fiance/ex-fiance? I tried to explain to her that I had no idea that he was in a relationship. He was the one who had approached me. She was having none of it. This bitch started leaving threatening notes on my car and stalking me at work.
• I moved a Lego guy from the Lego road onto the top of a Lego building. She threw me out of the house.
• My ex-boyfriend liked Nickelback.
• My now ex girlfriend lived 60 miles away and I would stay with her at least 5 sometimes 6 nights a week. I subscribe to Sports Illustrated and I got the annual Swimsuit Edition one week. I grabbed my mail after work, threw it on the passenger seat and began the drive to see her. I arrive, shower, and we go out to the car to go out to eat and she grabs the magazine, flips it over and screams "WHAT the FUCK is THIS?!" Taken by surprise, I kinda laughed and said "pretty obvious". She frrrreaked out, yelling, screaming, accusing me of cheating on her (with girls in the magazine), threw the magazine at me and told me to go home.
• She left a dead bird on my doorstep with a note, saying "This is what you did to my heart"
• She knew I wanted to break up with her. Things weren't working out and e both knew it. She wanted me to stay so she starting making up sob stories. These sob stories eventually turned into her being diagnosed with cancer. I believed her and she guilted me into staying with her. I eventually bit the bullet and ended it. I later found out it was all lies.

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That's all for this week. If you have a crazy story involving one of your exes, I want to hear it. Feel free to send them and any other stories of romance, anonymously if you prefer, to sean.joseph@outkick.com.

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