18. We All Lost

18. We All Lost

No one needed or wanted to see this man in a dress. For that reason, we have all lost. It makes you wonder what kind of bet this was. It could have been a sports bet, or something that came up during a game of poker. There's also the chance that this guy got hit with one of those surprise bets where someone knows information you don't, so they bet you on it. Then they pull out a newspaper. "I bet you Trump is separating undocumented children from their families." / "Stupid. I take that bet." *five minute later* "Can you button my dress for me?"

Let me get very woke for a second. You can tell me how annoying it is. This "punishment" is transphobic and homophobic, and probably another phobic too if I looked harder. Why is a man dressing as a woman a bad thing? My woke side calls foul!

NEXT

Did You Know...

I

In the US, the average spent on an engagement ring is $6,351 but how do these figures compare with our favorite celebrities? The answer: they don't. As the diamonds increase in size, obviously the price tag appreciates handsomely. Well, we've compiled a list of some of the most expensive celebrity engagement rings.

II

This list would be nothing without Kim Kardashian's rock from Kanye, which clocked in at around a cool $4 million when he presented it to her at his stadium proposal in October 2013. Unfortunately, though, the 15-carat sparkler was among the jewelry stolen during Kim's infamous Paris robbery in 2016.

III

Jennifer Lopez's husband Alex Rodriguez popped the question to the singer, and he really had to step it up to outshine her previous engagement rings—and wow, did he deliver. The baseball star proposed with a reported 15-20 carat emerald cut stunner set on a platinum band that was estimated at $5 million. It's getting harder and harder not to be fooled by the rocks she's got...

IV

It should come as no surprise that Beyonce herself totes one of the world's highest-valued diamonds. Weighing in at 24 carats, Jay reportedly paid around $5 million (now worth $6,047,013) for Bey's flashy emerald-cut ring back in 2008.

V

Anna Kournikova's relationship Latin music artist Enrique Iglesias since the early '00s has been one of the most lowkey celebrity relationships to date. That is with the exception of her $5,400,000 engagement ring that made headlines in 2004. Now, worth a whopping $7,443,596, the giant yellow stunner was spotted on Kournikova even during her tennis matches. (Pssst! It's rumored she got two rings from Iglesias. Prior to this, she sported an equally giant pink pear-shaped ring.)

VI

Clocking in as the most expensive celebrity engagement ring, Mariah Carey's 35-carat bling from ex-fiancé James Packer reportedly cost a cool $10 million. And the "Obsessed" singer seemed to be a bit, well, obsessed with the jewel. She continued to wear the ring over a year post-breakup, and didn't part ways with the bauble until May 2018, selling it to a Los Angeles jeweler for $2.1 million.

NEXT


Copyright © 2026 CultureHook