But the fashion designer's reported toy-boy ex Nick Gruber seems to have had more than a change of heart after he was seen kissing a woman this weekend.
The 22-year-old gay porn star was locked in an intimate embrace with erotic model Chelsea Heath on a beach in Los Angeles.
Moving on: Nick Gruber was locked in an intimate embrace with former Girls Gone Wild star Chelsea Heath in Los Angeles on Sunday
The pair was seen holding hands tightly on the sand before Nick removed his shirt and they went into the water to cool down.
Gruber is fresh from a stint in rehab after being arrest for cocaine possession and attacking another man.
The blond socialite was taken into custody in April for allegedly stashing the drug in his underwear and punching a 20-year-old male; he was said to have wanted to go on a big 'last night out' before getting clean, according to the New York Post.
New squeeze? The pair appeared giddy in each other's company as they frolicked on the sand in Marina del Rey
Klein, 69, has not publicly acknowledged a romantic relationship with Gruber.
But the designer is said to have supported him through several personal ordeals even after their split in January.
A protective arm: Heath grabbed Gruber tightly as they faced cameras on their beach outing
The designer had attended the same facility for his drug problems in 2003 and had arranged to foot the monthly $35,000 bill for his paramour.
He had also arranged to pay for Gruber's private jet transfer, in fear that if the porn star flew commercial he would be tempted to drink alcohol, according to the Post.
Rumoured romance: Calvin Klein, 69, and Gruber, 22 - pictured at an event in November - are believed to have dated for two years before splitting in January
Gruber also suffered from bulimia, which Klein reportedly helped him through.
Multiple reports suggest Klein and Gruber, who were frequently seen in each other's company, dated for nearly two years before growing apart and calling it quits.
