And as finding the right holiday gift for the lady in your life is about as daunting as it gets, FOXNews.com turned to the "Girls Next Door" star for some female advice.
“One of the best ways of figuring out the perfect gift is to pay attention to their personality," Madison told us. Your gift should only send the message ‘I love you.’ It shouldn’t say ‘I’m trying to change you."
Madison, who had the task of shopping for two special women this year (she made sure to spend the exact same amount on Hef's two other live-in girlfriends, Kendra Wilkinson and Bridget Marquadt) suggests sending out feelers to get a sense of what she really wants, and also tapping into your memory bank to recall hints she might have dropped.
But keep in mind that not everything on her yearlong drool list is appropriate for a holiday gift.
“Anything utilitarian is not romantic and gifts should be romantic. You don’t buy someone a gym membership,” Madison said. "I recommend getting jewelry even if you are just in a casual relationship. You don’t have to spend a lot of money. You can buy silver.”
And Hefner, the modern-day Casanova himself, agrees that shiny baubles are the way to go. Last year, Hef bought his gals diamond-faced Jacob and Company bunny watches that gave new meaning to the term Jingle Bell "Rock."
“Hef always gets us really amazing gifts. I tend to drop hints to Hef’s secretary," Madison said.
For those of you who don’t have a middleman or a clue where to begin, Marshall Cohen, chief analyst at consumer and retail market research information company NPD Group, has some other pointers.
“You better darn well make sure it's something she wants, not something you want for her. For example, lingerie is not a good idea unless she is clearly into it. Most women buy it for themselves because it’s the vision of how they want to look. They don’t want to know how you see them,” said Cohen.
Like Madison, Cohen feels that jewelry is a foolproof gift.
“The number-one emotionally attached gifts are jewelry as number one, chocolate as number two and apparel as number 3. Number 4 is coffee. Women love coffee.”
This season’s hot jewelry pieces include Kenneth Jay Lane cuff bracelets (which start at about $180), Gucci trademark earrings ($245) and Juicy Couture charm bracelets ($50 for chain, $15 and up per charm).
If bejeweling isn’t your thing, you might want to indulge her with a cashmere sweater from anywhere, Croco laptop case from Ann Taylor ($135), a Louis Vuitton zipped purse from eLuxury.com ($465) or a Betseyville by Betsy Johnson carry-on suitcase ($195).
If your lady doesn’t fit the typical recipient’s profile, taking the time to tailor a gift to someone’s interests can make the difference between a ho-hum gift and a home run gift.
“Kendra’s gifts are all sports-related, and everything I got Bridget is pink,” Madison said.
FOX Shops: Top Gifts for Every Lady in Your Life
Don't like Madison's and Cohen's picks? Here are some more ideas.
Wife: Spa packages are always welcome, especially the ones that include champagne lunch and a one-hour Swedish massage.
Grandma: Chances are your grandmother doesn’t need anything too extravagant, especially since most of her valuables have been preserved under plastic for half a century.
Instead, stick with tried and true staples, like silk scarves and sentimental picture frames. Our favorites include:
-Photo Heart Tote from RedEnvelope.com ($40-$49)
Jet-Setting Sister: The frequent traveler appreciates the little things in life … literally! Lightweight yet ultra chic gadgets and accessories will fly high with this gal.
-ChicBuds' dazzling Swarovski crystal earphones ($46). They even come with a retractable cord, making storage a cinch.
Female Best Friend: No matter how close you two are, your BFF won’t shrug it off if you get her a fern in a mug this holiday season. Opt for something tasteful yet naughty. You need something to laugh at 10 years from now!
-A groovy Victoria's Secret polka-dot babydoll nightie ($38).
-Stitch 'N Bitch ($15.50). This book is the modern girl's guide to the trendy pastime of needlework.
-Bath & Body Works' Sugar and Spice Sampler ($14.50). Give your best gabber three decadent lotions in fun fragrances Twisted Peppermint, Spicy Gingerbread and Wickedly Hot Chocolate.