Spencer Matthews is the reigning bad boy of U.K. reality TV who claims to have slept with 1,000 women

Credit: Alex B. Huckle/GC

He’s rich, handsome, went to school at Eton and will soon be related to Princess Kate. But that’s just about where the comparisons end between Prince William and Pippa Middleton‘s future brother-in-law, Spencer Matthews.

A former star of the popular U.K. Channel 4 reality show Made In Chelsea and the British version of The Bachelor, the 28-year-old Matthews – younger brother of Middleton’s hedge-fund manager fiancé James Matthews – is notorious for his hard-living, womanizing ways, once telling a girlfriend on the show, “It’s hard to respect you when you allow me to cheat on you.”

Since he shot to fame in 2011, Matthews has been pictured snorting cocaine, battled steroid addiction and revealed intimate details of his sex life in a 2014 tell-all memoir, Confessions of a Chelsea Boy. In fact, he’s just about the polar opposite of his modest and discreet elder brother, 40, who popped the question to Middleton, 32, amid the scenery of England’s beautiful Lake District on Sunday.

William, Kate and Mike Middleton (Kate and Pippa’s dad) have all publicly expressed their joy about the upcoming nuptials. Spencer has yet to comment, but he has appeared to tame his bad-boy reputation in recent months: He left Made In Chelsea last year and has since stepped out of the limelight to concentrate on charity work and more serious TV, recently profiling the downside of his steroid abuse in a documentary.

He’s also close to Kate’s younger brother James Middleton, describing him as his “beardsparation” on Instagram.

But for British TV viewers, he remains one of reality’s reigning rebels. Among his wildest moments:

1. The Full Face Slap

During his five series on Made in Chelsea, which details the partying and romances of a circuit of super-rich friends in west London, Matthews dated a series of women.

In season one, he set the tone for what would follow, brazenly announcing, “I wouldn’t sleep with anyone other than my girlfriend – at the moment.”

His serial bed-hopping came back to haunt him during the 2012 Christmas special, however, when furious costar Millie Mackintosh accused him of cheating on her friend Louise Thompson and slapped him full on the face.

(Warning: Clip contains explicit language)

“Okay, you believe what you want, if I wanted to sleep around I would have split up with you,” a stunned Matthews told Thompson. “You obviously have serious trust issues.”

2. The Steroid Scandal

In 2015, Matthews flew half way around the world to take part in I’m A Celebrity . . . Get Me Out Of Here! deep in the heart of the Australian bush. His jungle stint lasted a total of three days after he suffered severe withdrawal from steroids.

“Why did I leave I’m a Celebrity? The simple answer is that I screwed up, and have some explaining to do,” he said afterward in a statement, which went onto explain that he had used steroids to bulk up for a charity boxing match.

“Taking these pills was a serious error of judgment, which I hugely regret,” he added. “I have disappointed my family, friends and fans and would like to apologize.”

“I loved every minute of being in the jungle and wish the remaining contestants the best of luck. Hoping for another shot at it someday.”

He may be about to get his wish: Matthews has been clean of steroids for a year and recently filmed a documentary about steroid abuse for GMTV.

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“I’d love a second crack at the jungle,” he told GMTV host Piers Morgan. “My only three days were exceptionally fun. I had a really nice time.”

3. “23 Other Girls”

After spending 10 weeks in The Bahamas with 24 women, Matthews eventually selected model Khloe Evans as the winner of the British version of The Bachelor in 2012.

It wasn’t exactly the romance of the century: Two weeks later, Spencer was seen hanging out with his ex-girlfriend in London, while Khloe was pictured kissing another man in a nightclub.

Matthews then defiantly told Digital Spy that Khloe was a “mistake,” adding, “I don’t think she deserves a second chance.”

“It’s not like we had something extremely serious once The Bachelor finished,” he added. “We spent 10 weeks together, but I was also dating 23 other girls.

“I was looking forward to getting to know her better and possibly developing what could have been a relationship, but if you’re going to do that in the early stages it obviously wouldn’t have worked.

4. Bombshell Memoir

In his 2014 memoir Confessions of a Chelsea Boy, Matthews revealed details of his wild lifestyle – estimating that he had slept with around 1,000 women.

Among the more colorful adventures he details in the memoir: mistakenly hooking up with a “professional girl” in Johannesburg, accidentally dropping acid at a friend’s house in rural England and having to hide from Libyan assassins because he dated the same girl as the son of late Libyan dictator Colonel Gaddafi.

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“Look, in future if any terrorists ask for my whereabouts, don’t f**king tell them!” he recalled telling his close friends.

On a calmer note, Matthews did also reveal that he once played – and beat – Leonardo DiCaprio at backgammon.

5. The Bad Baseball Pitch

A 2014 Made In Chelsea: NYC special proved to be a quiet moment for Matthews on the romantic front, with him managing to score just a single kiss all vacation, despite ordering a vast amount of champagne and caviar to impress the heiresses of the Big Apple.

Worse, he also managed to commit the cardinal sin of American sports: Taking to the mound during a “friendly” game of baseball in the park, Matthews clutched the seam, tweaked the peak of his cap and sent down a pitch . . . underarm!