What Hugh Hefner's Playboy exes did next – from ghost hunting to fling with famous boxer and sisters' drunken brawl

SHE was once wed to the original playboy tycoon, but the widow of Hugh Hefner has found love once again.

Model Crystal Harris, 35, cosied up to actor boyfriend Ryan Malaty, 32, over Christmas in matching holiday jumpers.

The pair got together in July and have been on a series of lavish holidays together to Mexico, Egypt, the Maldives and the Cotswolds.

The romance came after Crystal's year-long relationship with engineer Nathan Levi – but the pair split in May 2021.

Her late husband died in 2017 after five years of marriage – but she wasn't the only love of his life.

The Playboy boss was known for surrounding himself with beautiful women amd had at least three girlfriends at a time sharing his $100million Playboy Mansion in LA.

We reveal how other Hef exes have fared after leaving the Mansion…

Kendra Wilkinson: From '1-minute sex' to real estate agent

The then 18-year-old caught Hugh’s eye when she was hired to perform as a naked statue at his 78th birthday party in 2004.

Afterwards he asked her to move in with him at the Playboy Mansion and be his girlfriend.

Glamour model and TV personality Kendra, now 36, said: “I moved in and weeks went by and I didn’t know that sex was involved.

"I knew nothing about Playboy. I’d just graduated high school.”

She said she would sleep with Hugh – but only after preparing herself first.

She recalled: “I was usually very drunk doing those evenings. I tended not to care about much until the next day. I had to be very drunk or smoke lots of weed to survive those nights.

“At about the minute mark, I pulled away and it was done. It was like a job.

"Clock in, clock out. It’s not like I enjoyed having sex with him.”

Kendra left the Mansion in 2008 after meeting her future husband, American footballer Hank Baskett.

She remained on friendly terms with Hugh and invited him to her 2009 wedding – held at the Mansion.

Kendra denied claims Hank had cheated on her with model Ava Sabrina when she was pregnant but they eventually divorced in 2018 after having children Hank IV, now ten, and Alijah Mary, five.

She went on to feature in US cable TV series Kendra On Top from 2012 to 2017 and the 2014 UK series of I’m A Celebrity, finishing sixth.

She is now studying to become a real estate agent, telling People: "I used to make so much money just stepping into a club, but those days are over."

Crystal Harris: 'Still healing' from life with Heffner

Model turned travel blogger Crystal had a bumpy ride with the Playboy tycoon.

She moved in with him in 2009 when she was 22 and he was 82, and lived with his twin girlfriends Kristina and Karissa Shannon.

In 2011 Hugh dumped the twins to marry Crystal – but she called off the wedding with just a few days to go.

During their brief split, Crystal confessed she had only had sex with Hugh once and it lasted “two seconds”.

She said: “I’m not turned on by Hef, sorry.”

But they were reconciled and eventually got hitched in 2012 in a lavish New Year’s Eve ceremony at the Playboy Mansion.

After Hugh’s death in 2017 Crystal said: “When I first met Hef I was this kind of insecure college girl.

"He taught me love. He taught me kindness. He gave me life. He really did.”

Even so, Hugh reportedly left Crystal nothing of his $50million (£38million) fortune in his will – apart from a $5million home.

Last month, Crystal visited the Playboy Mansion and reflected on her “contradictory” marriage to the Playboy empresario. 

She posted on her Instagram: “He was good to me in many ways, but in other ways he wasn’t. 

“I’m still healing from certain experiences.”

She soon dated Nathan Levi who designs spacecraft for Elon Musk and was a member of the team behind the successful launch of the reusable cargo craft SpaceX Dragon in March this year.

But the couple split after Crystal was diagnosed with a heart condition. 

She said last May: "I’ve found it best to just focus on myself lately. I recently ended a year long relationship and am just trying to get myself to a place of happiness and wellness.”

Izabella St James: $1,000-a-week 'allowance' to dog charity boss

Polish model Izabella – born Izabella Katarina Kasprzyk – emigrated to Canada with her family as a child, then moved to California to study for a law degree.

In 2002 she took a two-year break from her studies to move in with Hef.

Her biography describes how girlfriends were given a $1,000 (£770) weekly allowance and Hefner would fund unlimited plastic surgery.

She said: “Every Friday morning we had to go to Hef’s room, wait while he picked up all the dog poo off the carpet – then ask for our allowance.

“We all hated this process. Hef would always use the occasion to bring up anything he wasn’t happy about in the relationship.

“Most complaints were about the lack of harmony among the girlfriends or your lack of sexual participation in the ‘parties’ he held in his bedroom.”

Izabella, 46, now runs charity The Pug Queen, which rescues and rehomes neglected pugs all over the world.

She said: “If there’s a pug that needs to be rescued, everyone step out of my way. I’m not deterred by anything.”

US rapper Aaron Carter threatened to sue her for defamation after she accused him of abusing his pug Nala in 2020.

Carla Howe: Fling with famous boxer

The 31-year-old Brit and her sister Melissa lived with Hugh in the Playboy Mansion in his later years but Carla insisted their relationship was sex-free.

She told how she and her Playmate sister moved in in 2011 but soon became bored of life with the elderly Playboy chief.

Carla, originally from Slough, Berks, said a few years before his death: “He’s so old now I couldn’t imagine him trying to make a move.

"He has to walk with people around him because he’s frail.”

But she told of the strict rules girlfriends had to follow in the house.

She said: “When you’re here you have to be in by the 9pm curfew.

"You’re definitely not allowed male visitors. If you break the rules you get banned.

"Once you’re out, you’re out, you can’t come back.

“Hef’s wife Crystal went to do a DJ set miles away so she had to stay overnight. But she was still back by 2pm the next day.”

Carla went on to have flings with boxer Amir Khan while Melissa enjoyed dalliances with soccer’s Dele Alli and Ashley Cole.

Bridget Marquardt: I'm a paranormal investigator… Hef's ghost haunts his mansion

Bridget twice applied unsuccessfully to be in Playboy but was nevertheless invited to visit the Playboy Mansion and soon became a regular.

In 2002, after more than a year of visiting, she moved in and became one of Hugh’s girlfriends.

But Bridget struggled with criticism of the Bunnies.

She said: “The haters have so much time and so much energy – they call me fat and they say we’re sluts and gold-diggers – but I don’t allow myself to go there because one negative comment can stay with me for a really long time.”

She left the house in 2009 and is now working as a paranormal investigator and hosts the podcast Ghost Magnet.

In 2015 she got engaged to film director Nicholas Carpenter – son of astronaut Scott Carpenter.

Shortly before the death of her former boyfriend Hugh in 2017 she said he had frozen her out of his life.

Bridget, now 48, said: “I was still in touch with Hef – and then we kind of lost contact.

“I called and tried to go to the mansion earlier this year but I’m just getting the runaround.”

Bridget says she believes the late Hugh haunts the Playboy Mansion and last Halloween she and Playboy pal Holly Madison tried to contact him in a seance.

She said: “People ask me, ‘Do you think Hef is still at the mansion?’ and I say, ‘Absolutely’. I just feel like he is.”

Sandy & Mandy Bentley: Boyfriend jailed before lover shot dead

From 1999 to 2000, the twins – now 43 – lived it up as part of Hugh’s seven-strong harem and starred on the cover of Playboy.

But they soon irked Hef when he suspected they had boyfriends on the side.

His former girlfriend Izabella St James said: “From what I was told by the mansion staff, Sandy and Mandy caused Hef a lot of heartache.

“You’re not supposed to date other guys. Hef is very possessive.”

After leaving the mansion, Sandy began a relationship with millionaire Mark Yagalla, who lavished her with jewellery.

But in 2002 he was jailed for running a Ponzi scheme and Sandy was ordered to return $1million worth of jewels.

Her new boyfriend Michael Tardio was trying to find a buyer for the jewels when he was shot dead by a mystery assailant.

Kristina & Karissa Shannon: Arrested after a drunken brawl

The Michigan-born twins, now 32, joined Hugh in his sprawling mansion in 2008, after his top girlfriend Holly Madison moved out.

The duo left in 2010, but moved next door to stay with other Playmates.

Hugh said at the time: “The Shannon twins are growing up.

"They’re moving to the Playmate House with my blessing so they will be free to do other things.”

But the twins briefly moved back in with Hef when Crystal Harris called off her 2011 wedding to him.

In 2012 the twins appeared in Celebrity Big Brother and came fifth in the series but their various troubles with the law soon got in the way of their plans for showbusiness stardom.

Kristina was charged with drunken driving in 2016 after crashing a car while on her way with her sister to get a nipple piercing.

And in 2017 both sisters were arrested for domestic violence after they got into a drunken brawl.

Kristina punched her sister in the face while Karissa knocked out her sister’s teeth by throwing a security alarm at her.

Holly Madison: Split from music producer

Hugh's original “Number One” girl was working at US fast food chain Hooters when she met him.

In 2001, after a year of attending weekly pool parties at the Playboy Mansion’s grotto, 21-year-old Holly moved in with the tycoon.

In her 2015 autobiography, Down The Rabbit Hole, she told how Hugh held twice-weekly orgies at which he offered the girls sedative drugs.

Holly, now 42, soon became his favourite girlfriend and got a job at Playboy magazine as a junior photo editor.

But in 2006, when 80-year-old Hugh was found to be infertile, she decided to leave the millionaire.

She said: “This was concrete proof slapping me in the face that there was no future for me at the mansion.”

Holly married music promoter Pasquale Rotella and they had two children, but they divorced in February 2019.

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