The first time around, his intended called off their lavish wedding with just five days to go.
So perhaps it’s little wonder that Hugh Hefner was rather more cautious at the second attempt.
The 86-year-old Playboy founder has married blonde model Crystal Harris, in a small private ceremony with only a couple of dozen guests.
At 26, Miss Harris is more than young enough to be his great-granddaughter — and after she broke off their engagement in 2011, confessed: “I’m not turned on by Hef, sorry.”
She evidently had a rethink, however, and on New Year’s Eve became the multimillionaire’s third wife. The couple tied the knot under a giant arch of white and pink flowers at the Playboy Mansion in Los Angeles.
The bride, whose parents are British, wore what she said was a pale pink “mermaid” dress, a tribute to her love of all things Disney — especially the film The Little Mermaid.
Only around two dozen white chairs were set out for the ceremony and the new Mrs Hefner gave little detail away on Twitter, other than a flurry of messages that revealed her understandable excitement at her promotion from former Playmate to wife.
“Today is the day I become Mrs Hugh Hefner,” she wrote. “Feeling very happy, lucky and blessed.”
Both shared photographs of their big day on Twitter, with Hefner writing: “Crystal & I married on New Year’s Eve in the Mansion with Keith [his younger brother] as Best Man. Love that girl!”
After he had changed out of a dinner jacket into his more familiar purple silk pyjamas and naval cap, Hefner tweeted a second picture of the couple with the message: “Happy New Year from Mr and Mrs Hugh Hefner.”
The new Mrs Hefner tweeted a photograph of herself in her wedding gown, and one of the couple with Hefner’s new mother-in-law, who is still some 30 years his junior.
It was a far happier ending for Hefner than the first time he tried to marry Miss Harris, a psychology graduate who was born in San Diego but raised in the UK. In June 2011 she called off the lavish wedding in what she called a “change of heart”, just five days before she was due to walk down the aisle in front of 300 guests.
But after reportedly selling her $90,000 (Dh330,579) engagement ring for less than a third of its value, Miss Harris is understood to have returned to the mansion last year, where the couple reconciled.
In an interview, she said: “I needed to explore out there and take the time away [from Hefner and the Mansion].
“The time away really helped make me realise that where I’m meant to be is here with Hef.”