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:

Personalized Zippo Lighter: This is such a classic, old-school personalized groomsmen gift. We could totally see a smoking-jacket-clad Hefner passing these out to the guys. Plus, it’s pretty symbolic – the flame is guaranteed to never go out.

Cigar Humidor: Think back to the days of the old Playboy Clubs; the sophisticated members would all be sitting around drinking their martinis and enjoying fine stogies. The aficionado of cigars will really appreciate having a fine-looking and highly functional storage spot to keep his smokes fresh and crush-free.

Engraved Barware: We know the Hef drinks, we’ve seen him shuffling around many times with an adult beverage in hand, probably trying to self-medicate over the stress of juggling so many women. He’s done ads for Stoli and Bavaria, so he must like both vodka and beer. Presenting groomsmen gifts like engraved flasks, sets of shot glasses, or even retro cocktail shakers would be oh-so sophisticated in that rich, wrinkled, “I’m an octogenarian player” sort of way.