Chelsea Handler Confirms Hot, Rich, Mysterious Boyfriend

Chelsea Handler recently shared the first pictures of her new boyfriend on Instagram. The photos show them traveling together, including stops in Istanbul and Finland. Handler wrote about her experience learning about the history of the region during Ramadan, saying she gained a lot of knowledge. While she’s mentioned him before, this is the first time she’s revealed what he looks like. She playfully refers to him as “Cowboy,” though she admits he’s not a traditional cowboy.

Chelsea Handler met her current partner while playing blackjack. She didn’t have any money at the time and jokingly asked the man next to her, who was playing with a large stack of chips, if she could borrow a couple of thousand dollars. He obliged, she won the money back, and they started flirting, eventually exchanging numbers. He texted her the next day, saying she seemed like a fun adventure, and she responded with a link to a trip she was planning to Antarctica. To her surprise, he said he’d join her! They’ve continued traveling together since then. After ending her relationship with Jo Koy due to his traditional expectations, Handler seems to have found someone who better fits her modern lifestyle.

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2026-03-11 23:53