Does Your Date Think You’re a Gold Digger? 5 Things You Should Never Ask

by Rachel Greenwald - Matchmaker, Dating Coach and Author

Does Your Date Think You're a Gold Digger?  5 Things You Should Never Ask

“Gold Digger” is a crass label no one wants, but after interviewing 1,000 single men, I discovered it’s being applied to women more often than they think (and often unfairly). David, age 37 from Long Island, NY, described his recent date this way:  “She was looking for a ‘Perfect 10:’ the guy who’s a 5 on the looks scale with $5 million in the bank.”

As a dating coach and matchmaker, I’ve spent the past ten years conducting some unconventional dating research using an “exit interview” tactic I learned at Harvard Business School and applied to the dating world. I interviewed 1,000 men to find out what really happened after a dating disconnect. Many men described women whom they stereotyped as overly interested in money or overly focused on acquiring or maintaining a lavish lifestyle. In other words, they perceived certain women as “Park Avenue Princesses.” In face, The Park Avenue Princess was the #4 most common reason men lost interest in a woman after viewing her online dating profile, exchanging emails, or going on a first or second date.

Men have their radar up for gold diggers whom they think are looking to marry a lifestyle along with their man. In our shaky economy, financial security is more volatile now than ever before. Men are increasingly sensitive about finding someone genuine who will stick with them “for richer or poorer.” They often avoided a woman if she wrote in her online profile something along these lines: “I love shopping” or “I adore fine wines and champagne.” In an initial email exchange, men cringed if a woman wrote “I’m looking for a man who is generous” or “a man who has achieved career success.” Men believed these were proxy statements for “I want to be taken care of financially.” Of course, these were often misperceptions, but in the early stages of dating, perception is reality.

Men complained in my interviews about women on first dates who thought they were being subtle—but were completely transparent—when they tried to play “the money detective game” (a.k.a., “Are you rich or not?”). These gold-digger questions were reported most frequently:

1) Does your company give you stock options?
Gordon, a 36-year old entrepreneur from New York, NY, claimed to know every trick question in the gold digger handbook: “Women hear that I’m an entrepreneur, and they don’t know how to evaluate my financial situation. So they slip in proxy questions like ‘Does your company give you stock options?’”


2) What kind of car do you drive?
George, a 48-year old from Los Angeles, CA, says it’s very hard to find sincere women in L.A.: “I actually own two cars—a Prius and a Corvette– but I purposely drive my Prius on a first date to fend off the gold diggers.”


3) What does your dad do?
Paul, a 24-year old in Seattle, WA, is upfront during his dates about being unemployed. But women get confused when he takes them to expensive restaurants. He says, “So they ask me what my dad does, sniffing around to see whether I might have a trust fund.”

4) Which hotel did you stay at on your trip? Sam, a 31-year old in Dallas, TX, loves to travel and wants women to ask questions about the adventure side of his recent trip, not whether it was a luxury excursion: “When women ask me where I stayed, it’s obnoxious. The hotel is so irrelevant to my travel passion and so obviously an indication that she’s looking for a certain lifestyle.” He said one woman even asked him if he “flew commercial” on his trip!

5) Do you pay alimony? When you’re talking to a divorced man, the key is to focus on sympathy for what he’s gone through emotionally, especially if he has children. Ryan, a 55-year old from Providence, R.I., says he’s immediately turned off by the “alimony question” which several women have asked him on first dates. In his mind, that’s code for “How much money remains for me?”

And look out ladies for this Park Avenue Princess test I heard from Gerry, a 64-year old from Hartford, CT. He told me, “I like to mess with women when I think they’re gold-diggers. Sometimes I’ll let it slip (falsely) that I owe five months of back-rent or I maxed out my credit cards, just to test how fast they’ll look at their watches and calculate when they can politely go home.”

Men – both rich and poor– know that money is a factor on the dating circuit. But like a bad country western song, they just want to be loved for who they are. They don’t want to be taken advantage of financially or wonder if her feelings are genuine. Call me naïve or a hopeless romantic, but I’m betting that most of these supposed Park Avenue Princesses aren’t really screening their men for money. I think in many of these cases men reported, women were simply making casual conversation and sincerely trying to get to know their date better. But if a woman happened upon a few wrong questions inadvertently, the gold digger label was slapped on her fast by faulty, knee-jerk assumptions which a man made after watching too many bad reality TV shows. Now that you know what’s happening, you can simply avoid these types of questions so you’re not wrongly accused.

You’ll find all the other reasons men don’t call back (and what you can do about them) in my new book, Why He Didn’t Call You Back: 1,000 Guys Reveal What They Really Thought About You After Your Date.

Rachel Greenwald is the author of the new book:  Why He Didn’t Call You Back: 1,000 Guys Reveal What They Really Thought About You After Your Date. She is also the New York Times Bestselling author of Find a Husband After 35 (Using What I Learned at Harvard Business School). Rachel is a frequent relationship guest on The Today Show, The Early Show, CNN, National Public Radio, The Dennis Prager Show, and has been featured in Oprah Magazine, Fortune Magazine, The New Yorker, People, USA Today, and many others. She is a professional dating coach and matchmaker. Visit her website and ask Rachel a question at www.whyhedidntcallyouback.com

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