Womanizing, Partying & Business Backlash: 15 Secrets & Scandals Of Britney Spears' Wild New Love, Heir Harry Morton ‑‑ Could She Be Headed For Another Breakdown?
Sep. 15 2015, Updated 7:30 a.m. ET
Over the weekend, Britney Spears stepped out for a sushi date with 35-year-old Hard Rock heir and Pink Taco CEO Harry Morton, 34. But the womanizing party boy may not be the best match for the fragile 33-year-old mother of two, who is still under the strict conservatorship of her father, Jamie.
Harry Morton is in a happy mood one day after having a date with Britney Spears
Birds of a feather? Morton spent his younger years hanging out with notorious oil heir Brandon Davis, who is best known for his gambling habit and drunken bar fights. (According to the New York Post, they ended the friendship in 2005 over Davis' debt at Morton's family casino.)
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Already a womanizer in his early 20s, Morton is rumored to have dated Davis' ex Mischa Barton— who is reportedly struggling with sobriety these days— in early 2006.
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Morton's famous eatery isn't exactly family-friendly. In 2006, the mayor of Scottsdale, Arizona, slammed Pink Taco. "I really didn't want to see a business with that name opening anywhere here," Mary Manross said. The restaurant closed its Scottsdale outpost three years later in 2009.
Britney Spears leaves the Dorchester hotel
Spears adores her pups, but Morton may not be so animal friendly. In 2011, he angered activists by chaining a pink-dyed donkey in 85 degree-heat outside Pink Taco's Century City, California, location. Morton later agreed to stop using animals to promote his eatery.
Lindsay Lohan and Harry Morton leave her filmset together, Ca
In his most famous romance, Morton began dating a 20-year-old Lindsay Lohan in the summer of 2006. The pair partied around the world, from Los Angeles to London to Venice. He was also present when Lohan, who was hitting her first rock bottom, was hospitalized for "dehydration" that July. (Months later, she headed for rehab.)
Lindsay Lohan and Harry Morton looking in love in Hawaii
Morton and Lohan were reportedly so serious, he bought an engagement ring on a secret trip to Cartier in Beverly Hills. However, they split soon after in late September 2006.
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Onto the next! Morton had a sexy sleepover with party animal and Lohan's nemesis, Paris Hilton, just two months later in November.
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The younger, the better? Morton was spotted cozying up to Hayden Panterriere, then barely 20, in Malibu in August 2009.
Harry Morton is in a happy mood one day after having a date with Britney Spears
Reaching the A-list! Morton spent a flirty night out with Jennifer Aniston, 46, at the Sunset Tower Hotel in West Hollywood in September 2010.
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The handsome heir apparently has a craving for cougars. In January 2013, RadarOnline.com reported that Morton began dating a newly single Demi Moore, who was 19 years his senior.
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He became entangled in a love triangle when Moore began dating Morton's own father, Hard Rock mogul Peter, just months later.
Britney Spears enjoys lunch with her kids in Calabasas
Nearly a decade after his international clubbing bender with Lohan, Morton seems to be still be living the bachelor lifestyle. "I want to be talking about the party," he said in a recent Los Angeles Times article about his business goals.
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Friends fear that Morton's wild ways may be a risk to Spears' mental health.
"Her friends are mortified by her hanging out with Harry Morton because they know that she will get hurt in this one," a source exclusively tells RadarOnline.com. "Talk about a womanizer! Everyone is telling her to be careful."
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Also, pals say the pop star mom, who suffered a very public meltdown in 2007, may be too much for Morton to handle. "She has a lot of baggage and he is not equipped to deal with that," the friend adds.
Britney Spears heads to the gym
But there's little anyone can do. "Britney ultimately does whatever she wants and unfortunately, listens to no one about love," the source reveals.