Chelsea Handler Urges Kristin Cavallari to Treat Younger Boyfriends Like 'Prostitutes' After Ex-MTV Star Whined Over 'Paying for Everything'
Chelsea Handler gave Kristin Cavallari some very saucy dating advice.
May 27 2026, Published 2:20 p.m. ET
Chelsea Handler has shared some unconventional wisdom about how Kristin Cavallari should treat her younger boyfriends after her failed romance with TikToker Mark Estes, RadarOnline.com can reveal.
The 51-year-old comedian instructed the former reality star, 39, to start looking at boytoy romances like “prostitutes” after The Hills alum complained about how she "paid for everything" with the 26-year-old Montana Boyz hunk.
Chelsea Handler Has Paid the Bills With Men and Regretted It
Handler said 'it's ick' when she's had to pay for men while on dates.
During Handler's May 26 appearance on the MTV alum's Let's Be Honest podcast, the Chelsea Does star confessed that one of the "most important" things she looks for in a man is "someone who has their s--- together enough that they can afford to travel."
Cavallari jumped in to ask, "So, you would never pay for a guy?"
Handler responded that she has been the one paying the bills in a romance and "it's ick. It's not attractive," to which Cavallari agreed, "It's gross, right?"
"You think you can do it and that it's okay, and then you're like, 'I don't respect you,'" the former E! late-night host admitted.
Kristin Cavallari 'Paid for Everything' In Romance With Mark Estes
Kristin Cavallari paid for all of her dating activity with Mark Estes, including a trip to Greece.
"So funny because the younger guy that I dated, I paid for everything, and understandably so. He was 24," Cavallari explained about her seven-month romance with Estes in 2024.
"But like the one thing that I look back and it like p----- me off is that I paid, like, to go to Greece and like all these things, and I'm like, he took like half my AMEX points that f----- ," she said with a laugh.
However, Cavallari noted that she footed the bill for their entire romance, saying, "It still p----- me off to this day," to which Handler advised her to look at things in a more transactional way.
'Think of Him Like a Prostitute'
Handler told Cavallari to look at it like she's 'paying for a good time' with younger men.
"Well, it shouldn't. You have money. You're fine. You know who gives a s---. You're paying for a good time. You're renting a good time," Handler noted about boytoys.
"Think of him like a prostitute. You were just renting a good time," the Chelsea Handler: The Feeling star advised Cavallari.
Handler then noted that there's nothing wrong with spending money on a good time.
"It's like when I go to Vegas and if I lose money, which is rare, but when I do, I'm like, well, at least I rented a fun night. That's it. It's over. Move on to the next thing," she boasted.
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Kristin Cavallari Broke Up With Mark Estes So He Could 'Find Himself'
Cavallari said she knew that Estes wouldn't be a 'long-term' boyfriend for her.
Cavallari definitely got her money's worth with Estes, whom she called "the best boyfriend" she'd ever had during an October 2024 episode of her podcast when revealing that she broke things off.
"It’s hard because I broke up with Mark because I just know long-term it’s not right — and it’s not because of love lost or something bad happened," she confessed about the "sweet and supportive" social media star.
"I just know long-term he needs to experience life; he’s young … I started to feel the age a little bit with life experience," Cavallari described, as she is a divorced mother of three children she shares with ex-husband Jay Cutler.
"I look back when I was 24 and how much life has happened between then. Those are crucial years. Those are formative years. They’re when you find yourself, and he needs to be able to do that," she added about the decision to let Estes go.
