84-year-old Hugh proposed to Crystal Harris, 24, on Christmas Eve and Hugh's former girlfriend and one-time Playboy Playmate Kendra Wilkinson thinks the timing couldn't be better because Hugh is only now mature enough to handle marriage.
Kendra - who admitted she was surprised Hugh never married former girlfriend Holly Madison - told In Touch magazine: "We all thought it was going to be Holly! He's like any man - he was having fun and wasn't ready. I guess he was too young!"
Holly has previously revealed her dismay at the engagement, saying she is worried Crystal is using Hugh - who has been married twice before - to start her career and fears he could end up losing everything in an expensive divorce.
She said: "I've seen a lot of girls try to date Hef, and some have ulterior motives. I don't think it would be a bad idea for him to get to know her a little better. "I think it's possible Crystal could break Hef's heart. They could end up divorcing, and she could take half his money.
"I'm not jealous that he'd marry someone else. I just don't want it to be a girl who's using him to start her career. Basically, I think he could do better than Crystal."