True Romance: Simon Cowell Offered Six-Figures To Judge Couple Having Sex, Friends With Benefits Arrest & More

It's Thursday and you know what that means. It's time for some True Romance. We've got a packed one this week. We're going to go through a few stories and a couple of anonymous threesome tips in response to last week's column.

First up, a couple wanted their bedroom habits to be observed and judged by the one and only Simon Cowell. They're either very confident in their skills or were hoping to be trashed by the hard-to-impress TV talent evaluator.

The couple offered Cowell six-figures to break down their performance too. Where do you go from there? Well, I'm not sure where others would go, but we're going to take a look at a woman whose "friends with benefits" offer lander her a trip to jail.

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How does that happen? We'll get into that. It turns out she was using the term friends with benefits loosely. The police have a different term for what she was offering. One that includes a free trip to jail.

Who knew?

Then, before we get to the anonymous threesome advice, we have a potential feel-good story of the week, if only this guy would open his eyes.

He's having some trouble helping his coworker get back at her husband by sleeping with her. Something about being "in a relationship himself" or some lame excuse.

Let's get the weekly festivities going and be sure to follow along on Twitter

Simon Cowell Offered Six-Figures To Judge Couple Having Sex

Simon Cowell revealed during a podcast appearance this week that he was once approached by a random couple and offered him six-figures to judge them having sex.

That Simon Cowell from American Idol and countless other competition shows where he serves as a judge of talent. He revealed the offer on the How to Fail podcast, reports the NY Post.

"Then, one time, I was in a restaurant and this guy comes up to me and he said, ‘I love your show. Would you take a picture?’ [I say], ‘Sure,'" Cowell said. The man then introduced his wife before asking if he would "judge [them] having sex."

He didn’t believe the offer at first. He thought for sure they were joking and responded, "I’m, like, ‘Are you winding me up?’ They went, ‘No, we’ll pay you.’"

Cowell added, "[I said], ‘Well, how much?’ It was actually a lot of money. I thought, ‘Do I? No, I just can’t do it.'"

How much was the offer from the couple? It was $150k to watch and judge them having sex. Believe it or not, Cowell ended up not taking the couple up on their offer. That's his loss.

I know he's worth a ton of money and $150k ultimately isn't that much for him, although it could pay for an alleged cosmetic procedure or two, but it's his loss because of the experience he missed out on.

How many people can say they got paid to judge a couple's abilities in the bedroom?

I'm willing to bet the number is extremely low. For the record, if I was ever offered anything close to that amount of money to judge a couple having sex, my answer would be yes.

This Week in True Romance:

A woman was arrested for an alleged "friends with benefits" offer at a Palm Beach hotel

A 39-year-old woman was arrested at a luxury hotel in Palm Beach, Florida last month after her alleged "friends with benefits" offer wound up being investigated by police.

The Palm Beach Police Department, according to CBS 12, learned that a woman they identified as Alina Shimova was looking for "friends with benefits." What's wrong with that, you ask?

This friends with benefits arrangement, police say, came with a $3,000 price tag. That, in the eyes of the law, is something very different. So they had an undercover officer reach out to Shimova via text message.

The officer expressed interest in her "friends with benefits" offer and, according to the probable cause affidavit, she set the rate of $1,000 along with a rose emoji, which - you learn something new every day - is associated with sex work.

During further communication between Shimova and the undercover officer, she reportedly told him that there was a minimum of two hours required for these arrangements.

He proposed four hours, to which police say that she quoted him a price of $4,000 with, you guessed it, another rose emoji. The Palm Beach Police Department said they met at the hotel bar on the evening of April 17.

Shimova reportedly said, "everything goes and she doesn’t waste time." The undercover officer then asked about various sexual acts. She allegedly responded, "Yes, that would be so good."

The PBPD then arrested her. They reportedly found  five condoms, lubricant, and cash during a search of her bag. Shimova, CBS 12 reports, has been accused of offering prostitution.

It just goes to show if it sounds too good to be true, it probably is. I could be wrong, but this doesn’t sound like the ending to any friends with benefits story I've ever heard.

My coworker wants me to sleep with her to get back at her husband

From an apparent phony "friends with benefits" scam to an opportunity to be a good friend to a coworker. A man was approached with a simple request from one of his coworkers. Help her get back at her cheating husband by sleeping with her.

He was approached the other day at work by his coworker who he's calling Jane for the sake of the story. She caught her husband having a four-month affair with another woman.

He assumed that they would be headed for a divorce, but they're not. After getting caught cheating, her husband offered her a hall pass to "sleep with anyone any time."

"Jane decided that she wanted me to be her hall pass. She approached me last Friday and explained the situation to me during lunch," he shared on Reddit.

"She said she’s picking me because one her husband knows who I am and it would hurt him when she tells him it was me."

Obviously, he's ready to help a coworker in need out, right? Not exactly. He tossed out a couple of excuses as to why he wouldn’t be able to help her.

"I told her she was crazy and that I wasn’t going to sleep with her because 1. I’m in a relationship myself and 2. I don’t want to get involved with her drama," he wrote.

"She said she was going to tell her husband that she and I had relations anyway."

That sounds like a reasonable compromise, doesn’t it? He gets to help without doing a thing. His girlfriend has nothing to worry about. Not if you're this guy. That's not going to work either.

He's taking it to HR and hoping everything will work itself out from there. Good luck with that. Now you're getting called to explain yourself and there's going to be a whole headache surrounding them trying to get to the bottom of everything.

He would have been better off being a decent friend to his coworker and helping her out in her time of need. You never know when you'll be stuck in a similar situation and need their help. It's all about teamwork.

Threesome fantasy that his girlfriend can't stop thinking about

Now let's unpack the solid anonymous advice that hit the inbox this week. If you remember or in case you missed it, there was a story about a boyfriend sharing his threesome fantasy with his girlfriend in last week's column.

The girlfriend wasn’t into it at first, but found herself looking for advice on how to bring the topic back up with her boyfriend after being unable to stop thinking about it. I asked for some thoughts on it and got a couple of responses.

On the girlfriend threesome fantasy

- Anonymous writes:

If it’s with a partner, ensure your relationship is stable and trust is strong. If involving a third, pick someone respectful and compatible who understands the dynamic. Avoid close friends to prevent complications. Reallife threesomes may not match porn or fantasies. Awkward moments or mismatched chemistry can happen. My advice is to approach it with a sense of humor and be flexible.

Threesomes

- Anonymous writes:

It’s natural for her to feel a mix of curiosity, excitement, and uncertainty.

She needs to decide if she's considering it because she is genuinely interested or if she's only interest because her boyfriend wants to do it. ive been both interested and doing it for someone else. 

She needs to answer this- Is it really curiosity, fantasy, or something else? If she's into it i say go for it!

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That's all for this week. Solid advice and a thank you to those who hit the inbox. Have a great week. Follow along on Twitter and feel free to send questions, comments, stories, and whatever else you like my way.

The inbox is always open sean.joseph@outkick.com.

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Sean is a cubicle life escapee and proud member of OutKick's Culture Department. He enjoys long walks on the beach, candlelit dinners, and puppies - only one of those things is true.