50+ Dating Tips for Gold Diggers

Quick: a cougar with $100 bills dripping from her pocketbook is passing you by! Do you a) follow behind her snatching up the money before dashing off; b) catch a handful of the cash and return it to her hoping for a reward; or c) leave all of the money on the ground and "bump" into her by mistake before whisking her off her feet and charming her into a solid relationship that results in your becoming her sole benefactor in her will. If you want lessons in how to be a successful gold digger, turn to this list of more than 50 tips, all designed to get you rich quick.

The Hunt

Find yourself a sugar daddy or sugar mama by following this advice.

  1. Get your priorities straight: Before unleashing your seduction prowess, make sure you know exactly what you want out of your next relationship. A man worth $1 million or an international playboy worth $100 million?
  2. Make your list: Keep your little black book up to date by researching Forbes’ lists of the richest men and women, the world’s top hedgefund managers and Saudi princes.
  3. Stay organized: If you get caught dating more than one millionaire at a time, you’ll blow your cover and you’ll never be able to show your face at a major benefit again. Stay organized and avoid double booking.
  4. Become a stalker: Knowing the habits and schedules of your potential mates will make it easier to seduce them.
  5. Get a boob job: You have to look the part, right? Women should get a boob job so they’ll more easily fit in with all the other gold diggers clinging on to their society men.
  6. Set up a fake business or money story to hide behind: No one can accuse you of being a gold digger if you’re already wealthy, can they? If you’re actually quite poor, come up with a story about a dead uncle who left you all of his money or a fake enterprise a la Wedding Crashers to give you a solid cover.
  7. Get an invitation: Trying to sneak into a gala or the VIP room without an invite will call unnecessary attention to yourself and make everyone suspect your legitimacy as a rich, important somebody. Step on whoever you can to get a real invitation.
  8. Join aSmallWorld: See if you can join this social networking site that’s reserved for the international jet setting group. You’ll meet new prey and will learn about the hottest parties to attend.
  9. Advertise on Craigslist: Put up a posting that asks for someone who has a good education, a job in a prestigious field and likes to take vacations.
  10. Before you ask someone their name, ask if they’ll buy you a drink: That way, you’ll know straight up if your potential sugar daddy or mama is okay with spending money freely on you.
  11. Go to auctions where there is a minimum bidding price: Scrape together the cash or tag along with a rich friend to an auction or fundraiser that requires each party goer to spend a certain amount on tickets and bids.
  12. Become well-versed in issues of finance: If you’re only going to be talking with rich men and women, make sure you are current on the stock market, economy, and anything else high society or money-related.
  13. Offer to pay for the tip: Tsk-tsk’ing your date away from paying the tip while you whip out your roll of $5 bills will make you seem generous and independent. If you don’t at least pay for the tip, you risk looking like a mooch.
  14. Wear lots of perfume, cologne, jewelry and outrageously fancy clothes: To blend in with the other rich people, of course.
  15. "Forget" to bring your credit card: If all you bring to the bars or to dinner is a few dollars, your date will have to pay for both of you.
  16. Only pursue cougars and older men: They’re the only ones with real money anyway.

Fitting In

Gold diggers must fit in with the "in" crowd if they want everyone to believe they’re genuinely attached to their millionaire lover.

  1. Always own the newest model of everything: Show everyone you’re on the cutting edge by having the newest phone, latest clothes and all the best toys no one’s even heard of yet.
  2. Show off your lover’s money: Show off your lover’s success by bragging to everyone how rich you two are.
  3. Act very smart and put on heirs: To convince everyone that you’re disgustingly rich, tell everyone that you went to Yale and Harvard and that your family vacationed in St. Tropez and Palm Beach during your breaks. If they ask you your last name, just make up something that sounds rich.
  4. Play tennis: Even if you don’t really know how to play tennis, you should still try to hold your own against those rich socialites who were trained by the professionals.
  5. Beg for more money: You’ll need a hefty allowance to shop for clothes, a nice car and lots of presents for your generous date.
  6. Become intoxicated at each party you attend: This sort of behavior is actually encouraged at rich people events, so you’ll fit in quite well.
  7. Spend ridiculous amounts of money everywhere you go: Spending lots of money isn’t just for cars, clothes or vacations. Spend way too much at the grocery store, the gas station and the convenience store to prove to everyone how important you and your partner are.
  8. Wear fur and jewelry in the middle of the afternoon: Just in case someone pops by and you need to show off.
  9. Become friends with other rich men or women…just in case: Even if you’re technically taken, you can still flirt with Donald Trump and Stavros Niarchos just in case something "happens" to your lover.
  10. Know everyone’s financial history backwards and forwards…and repeat it back to them whenever you can: Flatter your new friends by revealing to them how much you know about their bankruptcies, wills, new business ventures, trust funds and stock holdings. They’ll admire your attention to detail.

Getting What You Want, or, Focusing on the Money

Being a gold digger isn’t always easy. If you start to lose focus because sex with a much older man or woman is less appealing than you thought, or if you’re actually bored all day while everyone else is at work, follow this advice to keep you going strong.

  1. Only think about money: Even if you’ve realized that you don’t actually love your new spouse or partner, focus on the money to make yourself feel better.
  2. Recite "Money can buy you happiness" over and over: This little mantra will keep you focused even when you’re in the depths of despair.
  3. Don’t get a job: No matter how bad things get, you can always find another rich lover, but never get a job. You’ll ruin your reputation.
  4. Set up an affair for your lover: That way, you can catch him or her red handed, and demand new presents if they expect you to forgive them.
  5. Make your lover jealous by flirting with other millionaires: Start a bidding war by flirting with other millionaires or billionaires. You’ll make your lover jealous, encouraging them to spend more money on you so that you’ll stay.
  6. Go over your list of ex-boyfriends and girlfriends: If you survived dating other old, crabby men or women, you can make this relationship work too. It’s all worth it in the end.
  7. Start stealing cash: Swipe $100 bills whenever you can so that you’ll always have a safety net just in case something happens.
  8. Take lots of vacations alone: Ask to go on vacations without your lover so that you can spend all of their money without having to spend any time with them.
  9. Visit the country house: Visit each of the country houses to "check on the servants" as a way to take a break from your sugar daddy or sugar mama without having to break up and lose the money.
  10. Have a child: If you’re afraid that your lover is about to dump you, get pregnant so that they’ll forever be tied to you financially.
  11. Refuse to sign a pre-nup: No matter what.
  12. Constantly take on new redecorating projects: Redecorate every room in every house that belongs to your lover, just to keep yourself entertained and to have something to talk about at the club.
  13. Go on another diet or exercise plan: If you aren’t happy, go on a more extreme diet or exercise plan to keep you distracted, make others envious of you, and spend more money on gurus, diet pills, gym memberships and spa detox retreats.
  14. Pay in cash: If you pay in cash, there’s no record of where you spent your money, so you can tell your lover that you gave it away to a beggar on the street when you really got a dye job.
  15. Plan lots of surprise dinners and special nights out for your lover: They will make you look like a caring partner, but you’ll be putting it all on your lover’s tab, of course.

The Break Up

Sometimes gold diggers have to deal with the painful break up of their relationship with the money and the will. Deal with death, divorce and separation by considering these last tips.

  1. Hire a lawyer to manage the break up: even if it was just a one night stand.
  2. Steal your ex’s Rolodex: That way, you’ll have all of their rich friend’s phone numbers for when you’re ready to rebound.
  3. Start dressing even more provocatively than you did before the break up: That way, your ex will want you even more and may want to reconcile. If not, they may feel guilty enough to give you more presents or concessions during a divorce.
  4. Don’t get too sentimental: Money and property are essential, so snatch everything up while you still can.
  5. Visit WealthyMen.com: Go to this site to move on and meet someone even richer.
  6. Barter for long-term settlements: If you’re in the middle of a divorce, keep your eyes on the long-term prizes, like vacation homes, private jets, stocks, and heirloom jewelry.

Your Heroes

Every gold digger needs to have a hero to look up to when times get tough. From Playmates to supermodels, these gold diggers went after what they wanted and got it every time.

  1. Holly Madison: Holly Madison is one of Hugh Hefner’s girlfriends who appears on the E! reality series The Girls Next Door. According to the show, Madison is Hefner’s principal girlfriend at the moment, though he has had numerous girlfriends over the years. When Madison and Hefner met, Hefner had seven other girlfriends, but after a couple of years of dating, Madison has to compete with only two other "official" girlfriends. Gold diggers can take tips from Holly Madison, who consistently drops hints to Hugh Hefner that she wants to get married, despite his reputation. Persistence is key, ladies.
  2. Heidi Klum: Most people know Heidi Klum as one of the sexiest and most successful Victoria’s Secret models of all time, but before her marriage to singer Seal, Heidi Klum was married to Flavio Briatore, who was 23 years her senior. Klum was still pregnant with Briatore’s child when she began dating Seal in 2004. Gold diggers can still take classy lessons from Klum, though, who announced her pregnancy on the same day that Briatore and Fiona Swarovski were caught kissing.
  3. Anna Nicole Smith: Though Anna Nicole’s life ended in tragedy, she was the ultimate gold digger and became a celebrity in her own right. After her second husband billionaire J. Howard Marshall, who was 89 years old when he married the 26 year old Playboy model, died, Anna Nicole Smith inherited his wealth. Soon after, she filed for bankruptcy but ultimately became a legend and millionaire in her own right.
  4. Heather Mills: Heather Mills is Paul McCartney’s ex-wife and one determined gold digger. During a nasty divorce saga, Mills demanded millions of dollars from McCartney, and according to Hollyscoop.com, she ultimately got $50 million out of the marriage and is now catching the eye of Donald Trump. Not bad for an ex-prostitute.
  5. Marla Maples: Marla Maples is best known as the former beauty queen who had an affair with Donald Trump while he was married to Ivana. The two eventually married, had a daughter named Tiffany, and of course divorced. Since then, Maples has appeared on WWF WrestleMania VII and on the TV show The Ex-Wives Club. With a little determination and strategic dating, you too can become as successful as Marla Maples.