Relationship Goals: 9 New Dating Rules For Wealthy Men

Flaunting your Ferrari. Not-so-humble bragging. Using your business card as a “pickup line.” A dating coach reveals the hidden pitfalls wealthy men must avoid to attract quality women.

“Start by approaching those two women,” I told my new client Jason as we walked onto EP & LP, a rooftop lounge in West Hollywood. “Show me what you can do.”

As a dating coach who serves as a wingman for guys in bars and clubs, I like to start a night out by assessing a client’s social skills. When he talks to women, does his vocal tonality project confidence or fear? Does he make good eye contact or stare at his shoelaces? Does he stand tall or slouch? I’m looking for behavioral blind spots that are hurting his love life.

Jason (not his real name), in his late 30s, is a fit, handsome, wealthy doctor. He walked over to two 20-something women, a brunette and a redhead, both wearing dark blue jeans and drinking dirty martinis. But instead of introducing himself or just saying “hello,” he handed them his black-and-gold business card. “I’m a plastic surgeon,” he said with a cocky nod. “A Beverly Hills plastic surgeon.”

The women seemed confused at first. Was he trolling for new clients—a chin to lift, a tummy to tuck? The redhead self-consciously covered her freckled nose.

Then they realized: this was his “pickup line.” They looked at each other and giggled, laughing at him, not with him. After a couple minutes of conversation, the brunette said, “Nice meeting you,” which is code for “not interested.” They left. Approach rejected.

I took Jason aside and told him why the women headed for the (Hollywood) hills. “You were straining to impress them, and it turned them off,” I said. “When you lead with your money or your cool job, it tells a woman that you’re not enough for her as you are—that she’s out of your league. That kills attraction.” Plus, I added, it insults her because it implies that she can be had with the flash of a business card. “You need to buy into the idea that you’re enough for any woman.”

Jason isn’t the first wealthy guy to fall into this trap. Many men date with their head up their assets. Sure, money can give you an edge with some women, but if you flaunt it the wrong way, it mostly turns them off.

A guy will make this mistake for a couple possible reasons. He may feel unworthy of beautiful women, so he uses his money and status to compensate for what he feels is lacking. Or he may be buying into the myth that all girls want rich guys—that the road to their hearts is paved with Lamborghinis and lavish meals.

Having financial freedom is a nice bonus, but as I’ve learned studying dating success for a decade, quality women will like you for YOU.

From the first approach to the first date, here are nine rules wealthy men should follow to sidestep these traps and take their love lives to the next level.

Make a New Investment

There’s something valuable you must invest in, and it’s not a hedge fund, commercial real estate, or artwork: It’s yourself. Fully buy in to your value as a man, because if you don’t, women won’t either. Try an exercise I give my clients: Grab a pen and paper and list 25 qualities that make you a great dating decision for a woman. Don’t edit yourself. It can be any trait you like, great or small. (“I have a dry sense of humor,” “I’m a great dad,” “I’ve memorized every line from ‘Caddyshack.’ ”) This will connect you to the value you offer at your core. Because women fall for the man, not the mansion.

Let Her Discover Your Resources

Rather than crowbarring into the conversation details about your career or lifestyle, let her discover them. For instance, just minutes into meeting a man, most women will ask, “What do you do?” That’s a green light to open up about your career. (It would be impolite not to.) But when you do talk about your awesome job/calling/life, make sure you…

Play Up Your Passions, Not Your Portfolio

Maybe you like to swan-dive into your countless stacks of gold coins, like Scrooge McDuck. No judgment here. But that’s not the side to show women. Instead, convey your passion for what you do, or for how your wealth lets you serve others. Passion and generosity are very attractive traits. What do you love most about your career? How does it make you feel? Who does it let you help? How does it feel to help them?

That night out in Hollywood, Jason, my plastic-surgeon client, met a brainy, beautiful woman with dark, glossy hair. She sat in rapt attention as he spoke honestly about how fulfilled he feels when reshapes someone’s crooked nose or grafts healthy skin onto a burn victim’s neck. “I love helping people feel more confident about themselves and more beautiful,” he told her.

Women want a man who has passion for what he does, and who gives back to others.

Don’t Overspend

A client once came to me unable to get a second date with women. “I don’t know why,” he said. “I take them out for big, expensive meals, and they ghost me.” That’s largely why they ghosted him. A three-course dinner is a big first-date commitment, and the hefty check can make a guy seem try-hard. Instead, stick to drinks on first dates, and keep the tab to about $100. Spending much more than that is too much, too soon.

Don’t Attract. Connect.

Men obviously want to attract women. But if she’s on a date with you or has been talking to you for a while in a bar, she already finds you attractive. What women really want is to connect. Here’s a mission I give to my clients that you can try. I point to a woman, tell him to approach, and he has five minutes to find out what makes her fascinating, intriguing, unique. When a woman feels you “get” her, she’ll feel connected to you. And if she feels connected, she’s much more likely to be attracted.

Master the Humble-Brag

“Humble” is the key word here. Humility lets you show off without being a show-off. I worked with a guy who coached a Hall-of-Fame golfer. Women found this detail about him impressive, but they were more impressed by the way he shrugged it off as no big deal: “Hey, he hit the shots that won the Masters. I just helped a little.”

Don’t Buy Her a Drink…Yet

Never open a conversation with the words, “Buy you a drink?” It makes you predictable and ordinary, and women want extraordinary men. Instead, talk with her for 5 to 10 minutes and establish a rapport. Once you like each other a bit, by all means—be a gentleman and buy a lady a cocktail. Most men do it to keep her there. You’re treating her to that vodka-soda because you enjoy her company. She’ll feel that genuine connection and you’ll stand out.

Tell a Good Story

As humans, we’re hard-wired to love a good yarn. Storytelling makes you more charismatic. It also lets you take the same attractive traits that made you wealthy—your drive, your determination, your vision—and weave them into anecdotes. Jason has a story about the time in med school when he tried to do an all-nighter but passed out at dawn. He woke up halfway through his final exam and sprinted to the classroom to beg his professor for a make-up test. Why is this a good story? Because it shows both his drive to achieve and his vulnerability—two qualities ladies love in a man.

Leave Your Business Card at Home

Because when you see a woman you want to talk to, the best pickup line has nothing to do with money. Try a simple, honest, “Hi. I saw you and wanted to meet you.”

That will make HER feel like a million bucks.

Dating coach Connell Barrett is the founder and executive coach of To book a free strategy call with him, go to