True Romance: Proud Gold Digger Inspiring Others To Date For Money, Dating A Married Man & Getting Cheated On

Welcome to the latest True Romance. This week we have some touching news on the celebrity romance side of love. A couple made it over an important hurdle.

But first I wanted to take you behind the curtain just a little. Don’t worry about that locked door in the very back. There's nothing in there you need to concern yourself with.

I wanted to share some of what goes into making this happen. I head into each week wide open. I don’t say this week we're focusing on this and that over there is off limits.

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I keep an open heart and an open mind. I let the love and the romance find me. If I see something I'll make note of it and make sure to come back to it later in the week.

Is it a perfect process? Who wants perfect? Not this guy. I want fun and I want something that's going to provide a few minutes of entertainment. That's why we're here.

Sometimes we get heartbreak and sometimes we find magic. It's a journey, one that keeps us on our toes. That leads us to the celebrity couple and them making it to the next level in their relationship.

Last weekend was a big one for Timothee Chalamet and Kylie Jenner. The lovely couple attended the Golden Globes together where Kylie elegantly gave double middle fingers and received a shoutout from Timothee as he took home an award.

But that's not the news we're here for. We're here because she finally made an appearance on his Instagram. That's right, after all this time together and being spotted together out in public, Kylie finally made it to his Instagram.

Well, her hand holding part of his award did anyway. That's a modern-day romance at its very, very best and don’t you dare buy into any rumors about these two calling it quits.

If you're a frequent reader of the column you know by now I can’t let us get too high or too low before we dig into the rest of the romance. We have to go into it as close to even as possible. Otherwise, we've tainted the entire week.

You don't want that and neither do I. So I'm forced to bring us back down to as close as even as we can get by informing you that Todd Bridges and his wife Bettijo are getting divorced.

That hurts me as much as it does you, trust me. But now we're not going into this in the clouds with the news that Kylie Jenner's hand appeared on Timothee Chalamet's Instagram.

We have an inspirational gold digger to get to. She's proud and wants to show others that you, too, can date for money and find the one, as she has. She's engaged to a wealthy older man who knows she's with him for his money. He doesn’t seem to care.

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Proud Gold Digger wants to inspire others to date for money

Being a proud gold digger doesn’t mean there isn’t also love there. I'm as skeptical as anyone who says they got into a relationship with an older, wealthier man for his money.

But what Paige and Jaime have is real. How do I know? Because Paige lost one of her closest friends over this relationship. Someone she had been friends with for a long time.

The best friend of 20 years didn’t understand the love between a 29-year-old woman and a 55-year-old man with a ton of money. This romance didn’t start with her looking to become a gold digger.

It was Jaime, who saw Paige on social media and slid into her DMs. He wanted to get to know her and sent her his phone number right away, according to Love Don't Judge.

A proud gold digger wants to inspire others to date and marry wealthy men. (Image Credit: Getty)

Paige conducted a background check on this man in her DMs. She noticed he was wealthy, had fancy cars and a beautiful house. In other words, he was just her type.

Call her a gold digger all you want. She doesn’t care and wears the title as a badge of honor. She admits that they probably wouldn’t have started dating if Jaime wasn’t wealthy, but he is, and now she's in love.

The two began their relationship in November 2024 and by April 2025 they were engaged. They had found their soulmates and if piles of money are what made that take place, so be it. 

After finding her Mr. Right and all his money, Paige hopes to inspire others to "bag the boss." She provides a how-to on how to land a man that can take care of all her financial needs.

While an old friendship has come to an end, both of their families support the relationship, even Jaime's two adult sons, ages 27 and 25.

This is beautiful. A woman who has no problem being a gold digger for the right wealthy man and a wealthy older man finding a woman he can settle down with. There's no need for a prenup here. This is love.

This Week In True Romance

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A friend is dating a married man

What do you do when your friend, a 20-year-old woman, is dating a 35-year-old married man with kids? I know what I would do, grab some popcorn and enjoy the show.

That's not what this friend is doing. She's pretending to be a good friend by taking her concerns to the experts in the comment section of Reddit.

In other words, she wants in on the drama. Her refusal to allow this romance to take its natural course by attempting to force her own will on it is disturbing.

The two lovebirds have been dating for around six to eight months and, wait for it, the wife just found out. The friend isn’t sure what to do.

A concerned friend is trying to weasel her way into the middle of her friend's relationship with a married man. (Image Credit: Getty)

"Yesterday his wife found out and things got real bad. What shocked me is that she is considering getting married to him. When I asked about the kids, she said they like her so it should be fine," the friend wrote.

"I’m really worried. If he can cheat on his wife, what’s stopping him from doing the same to her? She’s only 20, still studying and doesn’t seem to be thinking about the long term consequences."

She added, "She’s smart and has her whole life ahead of her but she’s too emotionally invested to listen right now. I’ve tried talking to her calmly but nothing is getting through. How do I help her see reality without losing her as a friend?"

The reality? Here's the reality. It's not up to you as her friend to get involved. Grab the popcorn, sit back and watch, then if she needs someone, be there for her as her friend and maybe a short, but passionate lesbian relationship to get her back on track.

That's all. And who are you to say that he's not cheating on his wife with a younger woman because the younger woman isn’t the one for him? These two could have a long-lasting loving marriage. If not, see the paragraph above.

What was the wildest way you found out you were being cheated on?

So far this week we've managed to avoid the absurd. That is about to change. All you need is a thread about the wildest ways people found out they were being cheated on to accomplish that.

Prepare yourself because we've got double lives with multiple boyfriends and tasteful nudes with a photographer that went too far. Buckle up, our weekly Reddit thread is here for a ride on the absurd highway.

If you can relate to any of these, I want to hear about it. Let's go:

• She didn’t realize that her iPhone messages were also synchronized to her Mac, which I was using to stream movies on. I saw text popping up with her writing to her ex
• Her other boyfriend (who I didn’t know existed) and I had a mutual friend who put two and two together and told me. I said I wanted to meet him so he called him over. We talked out some things and then called her together at my suggestion. Good times were had by all
• He was drunk at his 21st and while joking around with his friends he started listing off all the women he’d slept with in the last year. I was standing right there and we’d been dating for two years at that point.
• One of her friends was a photographer and wanted to do 'tasteful nudes' which apparently includes penetration! And multiple days of getting the right shot...
• My 9 year old son told me that there were strange men in the house when I was away working. She'd been at it for years. It's horrible to deal with at the time, but honestly, it's such a relief to be rid of such a toxic mess.
• Date night cancelled day-of. I decided to make it a guys night to see the new marvel movie at the time. As we entered, I saw her sitting it the theatre snuggling up with a guy. Our seats were a few rows back, saw them kiss a couple times. When we all left at the end of the movie they were exiting their aisle as we walked down the stairs. She absolutely froze when she saw me. Blocked her on everything while I’m the in parking lot
• Not me but my dad. His girlfriend at the time had been cheating on him with his friend, who didn’t know they were in a relationship. My dad found out when his friend told him he was gonna propose to her
• After his company Christmas party I stayed over at his place. Got up the next morning and came downstairs to find his girlfriend cooking breakfast for him. Needless to say she and I were both pretty shocked.
• Broke up with me and as I was going though deleting her socials I noticed a post she made on her snap story that was her and a guy with a post saying "with my king", post was made two hours ago and had only broke up an hour ago
• My old barbershop… Was talking to my barber about her, and one of the other barbers overheard. We ended up finding out it was the same chick
• Happened to my cousin too. Came back from deployment, got a std and confronted wife about it. She confessed to sleeping with multiple men. I knew he was doomed when he called to tell me he was getting married and joining the army in the same sentence.
• He sent me a pic of the dog while I was away with a text that said "look how cute she looks" like 3 weeks later I went back to the photo to show a friend and upon looking at the photo again I noticed a pair of women's boots in the background by the door.
• I was out at a bar with some friends, when I started talking to the people next to me. They were wearing our towns local social sports club shirt. So I asked them if they knew my wife, who was in the club. They responded with "yeah I know her, I hear she is cheating on her douche bag husband." I then reply "I am her husband"

Sugar daddy-Bellamy Brothers

We're going to end things this week with a song. A song that I had never heard before, but is as romantic as they come. It's called Sugar Daddy by The Bellamy Brothers.

- MP from Staunton, Virginia writes:

Sean, enjoyed the Reddit thread in True Romance about sugar daddies. It reminded me of the classic country song "Sugar Daddy" by the Bellamy Brothers. Give it a listen if you aren’t already familiar with it. Keep up the good work.

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That's it. What a way to wrap up the week. Let's do it again next week. As always, you can reach me, anonymously if you prefer, at sean.joseph@outkick.com. Again, go follow along on Twitter and on Facebook.