Joshua Goldman
Joshua Goldman
min read · August 10, 2025 · Entertainment

Bethenny Frankel's Hilarious AI Date Picks: From DiCaprio to Bezos!

Bethenny Frankel has listed the celebrities artificial intelligence suggested she should date in a funny new video; pictured in May

Bethenny Frankel Exposes ChatGPT's Blunders: Dating Suggestion for 54-Year-Old Women!

In a hilarious new video, Bethenny Frankel took to Instagram on Sunday to reveal the top five matches suggested by her artificial intelligence, ChatGPT. The 54-year-old media personality couldn't help but poke fun at the absurdity of it all, leaving her fans in stitches.

Leonardo DiCaprio: The Unexpected Pick

On Sunday the 54-year-old media personality took to Instagram to share, 'Someone from my team just sent me the top five matches for me on ChatGPT. Let me tell you the top three'

The first name on the list was none other than Leonardo DiCaprio, who has been making headlines for his romantic escapades with younger women. Bethenny jokingly exclaimed, "Yes, I know I'm only 38 years too old for him!" She added with a wink, "But if he had some sort of breakdown, went to the Hoffman Institute, and came out as a 'Jesus' type – glowing, emotional, and ready to commit, maybe we'd have a chance!"

It's worth noting that DiCaprio is currently in his 50s, despite being known for dating women in their 20s. But who knows? Maybe ChatGPT was trying to be adventurous!

Bradley Cooper: The 'Love' Connection

The first familiar name she dropped was Leonardo DiCaprio, who is known for dating women in their 20s, despite turning 50 last November; pictured in July

The second name on the list sent fans into a frenzy – Bradley Cooper! Bethenny revealed that she thinks Cooper and his current girlfriend, Gigi Hadid, are an amazing couple. "I love them together," she said. "They're maintaining their privacy, they're beautiful, cool, and chill." But if things didn't work out between them, Bethenny jokingly offered herself as a potential match for the handsome actor.

Jeff Bezos: The Unlikely Suitor

The third name on the list was none other than Amazon's Jeff Bezos, who recently married Lauren Sanchez. Bethenny explained that she doesn't think they would be a good match, citing their busy schedules and talkative nature. "I'm in bed," she quipped, "and I don't think we could ever turn off the switch on work and Amazon products!"

Bradley Cooper, pictured with girlfriend Gigi Hadid, was also among the matches ChatGPT suggested for Bethenny

Fans Weigh In: The Suggestions

Bethenny's fans took to the comments section to share their thoughts, with some suggesting that Keanu Reeves or Donald Trump Jr. would make great matches for her! One fan even joked that she needs someone funny and authentic – preferably a water sign or earth sign who will bring loyalty and stability.

Another fan chimed in, "I see you with a man who is so confident and has done it all and is so in love with you... An older man who can be flexible and is super easygoing. Who he is? Your guess is as good as mine. But not a celebrity... God no!"

Billionaire Jeff Bezos, who is married to Lauren Sanchez, was also on the short list; pictured in December 2024

Bethenny's Reaction: The Blunders of ChatGPT

As the comments poured in, Bethenny couldn't help but react to the absurdity of it all. "But for one and two, doesn't ChatGPT look at who someone has historically dated, based on age?" she asked, laughing. Her fans were equally amused by the blunders of ChatGPT.

The video ended with Bethenny's signature humor and wit, leaving her fans eager to see what other hilarious moments will unfold in the future. Will we see Bethenny Frankel take on one of these unexpected matches? Only time will tell!

Readers' Reaction:

  • "This might be the best ChatGPT use – at least it's funny!"
  • "I think Keanu Reeves would be an awesome pick if his current relationship doesn't work out. He seems like a down-to-earth, nice guy!"
  • "You need someone funny and super authentic – and a water sign or earth sign will provide loyalty and stability."
  • "I'm holding out for Donald Trump Jr. for you," added one fan with a laughing emoji.

Share Your Thoughts:

What do you think about Bethenny Frankel's ChatGPT blunders? Do you have any suggestions for her next match? Let us know in the comments!