Still chasing the girls like a young whippersnapper, the 88-year-old Hugh Heffner is once again set to tie the knot with his on-again, off-again girlfriend, Crystal Harris. This makes “The Hef” our Marrying Man of the Month, although we’re not entirely sure the nuptials will go off without a hitch. You see, Heffner and the 26-year-old playmate are engaged to each other for the second time around; the first engagement was broken off by the bolting bride-to-be just days before the wedding which was originally set for 2011. However, in recent months, Harris has moved back into the Playboy Mansion and the two have reportedly been spending more time together. Despite the 60+ year age disparity, Harris has mentioned in the past that “she is the one keeping up with Hef.” Sources confirm that the May-December romance will culminate with a wedding at the Playboy Mansion this New Year’s Eve with family and close friends in attendance. So, if Hef were to have a posse of groomsmen, what kind of groomsmen gifts do you think he’d give? Here are our top picks:

An on-again, off-again Hollywood couple has decided to make it official . . . soon. According to reports, Justin Timberlake and Jessica Biel, became engaged during the recent winter holidays and are planning a summer wedding. While you guys aren’t going to be impressed at all with the frilly bride-to-be details, like the rumored designer of her wedding dress or the history behind the vintage-looking engagement ring, there is one ‘cool dude’ aspect of the engagement to date – the pair became engaged in Jackson Hole, Wyoming while shredding up the slopes on snowboards. In our opinion, that sure beats popping the question to your girl wearing a stuffy suit in some fancy restaurant. That Jessica is one cool chick!

Paul McCartney has a ‘Ticket to Bride,’ yeah; he’s got a ticket to bride! On Sunday, October 9, 2011, the former Beatle married heiress Nancy Shevell in a civil ceremony at Old Maryelbone Town Hall in London. This is Sir Paul’s third marriage, the first, ended sadly when his wife Linda died from breast cancer in 1998. The second ended scandalous in divorce from Heather Mills who slung plenty of mud and demanded a massive settlement.

Hard to believe, but KISS bassist Gene Simmons may actually settle down and marry his long-time steady, Shannon Tweed. Reports from the Daily Mail are saying that the 61-year old rocker and confirmed player is finally ready to wed his girlfriend and mother of his two children after a 28 year relationship!

Congratulations are in order on many levels for actor and now groom, Ryan Reynolds. Not only did he tie the knot with the lovely actress Blake Lively; perhaps, more impressively, he pulled off a celebrity wedding right under the nose of the unsuspecting paparazzi. The surprise ceremony took place on Sunday, September 7, 2012 at Boone Hall Plantation in Mt. Pleasant. Interestingly, this is the same location where “The Notebook” was filmed in 2004. It wasn’t until five days later that the two filed for a marriage license in Charleston and were legally married the next day, September 14th.

September has been a bit dry for celebrity bachelors signing up for the big M so we've decided to make our Marrying Man of the Month this time around, Prince William of Wales. "Is he" or "isn't he" has been the topic of conversation for years about when this heir to the British throne will finally settle down. After a courtship of more than 8 years, speculation about an engagement to his girlfriend, Kate Middleton, is reaching a frenzied pace with royal watchers (and even the rest of us). While there has been no official statement coming from the couple, the Queen or the House of Windsor, the gossip magazines and rumor mills are still churning full speed with the hopes that a royal wedding will soon occur. Britian's own online rag, "News of the World", has recently come out and said that the two will indeed wed in the summer of 2012 to put the spotlight on England right before the Queen's Jubilee and the Summer Olympics in London.

Status update: Married. That’s the message Mark Zuckerberg sent out hours after marrying his girlfriend of eight years. Zuckerberg, the 28 year-old who took Facebook public at $104 billion a couple weeks ago, tied the knot with Priscilla Chan, a recent medical school graduate, in a surprise ceremony that to place in the backyard of their Palo Alto home.

Probably singing “My Prerogative,” during the proposal (just a crazy guess), singer Brown and Alicia Etheridge are going to make it official after a two-year engagement. The couple, who also have a young child together, will be tying the knot as part of a business-pleasure trip to Hawaii. Brown has a Father’s Day gig in Honolulu, Hawaii and is parlaying a walk down the aisle on June 15th as part of the trip.

Redemption and forgiveness, those are good old-fashioned family values -- values you would expect from a sound and solid Marrying Man of the Month. Apparently Bristol Palin, daughter of past VP candidate Sarah Palin, is applying these moir_s of morality by taking back her baby-daddy, Levi Johnston after they'd been separated since the birth of their baby. You heard it here first (okay, maybe not first), but Levi is still our Marrying Man of the Month!

Looks like Alec Baldwin has made a bold move, and we’re not talking about playing ‘Words with Friends.’ Reps for the mouthy, trash-talking celeb have confirmed that the just turned 54-year-old 30 Rock actor popped the question to his 27-year-old girlfriend, Hilaria Thomas. Yes, they are getting M-A-R-R-I-E-D and that’s worth at least 9 points.

Marrying Man of the Month has been busy keeping up with all the celebrity wedding and engagement news that has been buzzing about. Most recently, Us Weekly magazine reports that actress Megan Fox is engaged to her long-time, on-again-off-again boyfriend, Brian Austin Green of " Beverly Hills 90210" fame. The news has been confirmed by the actorsÍ reps and Fox teasingly told E! Entertainment News tonight that the two will marry when ñthe stars align.î

An on-again, off-again Hollywood couple has decided to make it official . . . soon. According to reports, Justin Timberlake and Jessica Biel, became engaged during the recent winter holidays and are planning a summer wedding. While you guys aren’t going to be impressed at all with the frilly bride-to-be details, like the rumored designer of her wedding dress or the history behind the vintage-looking engagement ring, there is one ‘cool dude’ aspect of the engagement to date – the pair became engaged in Jackson Hole, Wyoming while shredding up the slopes on snowboards. In our opinion, that sure beats popping the question to your girl wearing a stuffy suit in some fancy restaurant. That Jessica is one cool chick!