Womanizing, Partying & Business Backlash: 15 Secrets & Scandals Of Britney Spears' Wild New Love, Heir Harry Morton ‑‑ Could She Be Headed For Another Breakdown?

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.

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.

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.

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.

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.)

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.

Onto the next! Morton had a sexy sleepover with party animal and Lohan's nemesis, Paris Hilton, just two months later in November.

He became entangled in a love triangle when Moore began dating Morton's own father, Hard Rock mogul Peter, just months later.

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.

But there's little anyone can do. "Britney ultimately does whatever she wants and unfortunately, listens to no one about love," the source reveals.