THE BLOG
03/16/2016 03:48 pm ET Updated Mar 16, 2017

She Said One Thing to Me on a Date - And I Went from Broke to Ballin'

Women often complain that the men they date don't listen. Often you'll say something important, or offer a really good piece of advice, and it just doesn't seem to sink in.

But more than you might realize, it does.

And it can utterly affect a man's mindset and entire direction in life.

A few years ago, I was dead broke. I had a great education and a moderately successful Hollywood career but it all came crashing down with a divorce and the death of the genre of film I had been writing.

I had started dating but felt pretty lousy about myself. My friends were all pretty well off. And I was trying to figure out what I could do with my talents, if anything.

One evening, while scrolling around an online dating site, I get a note from a woman who says her "friend" wants to meet me.

I write back that I would rather meet someone directly here - I know nothing about her.

"Trust me, you want to meet this woman. You've won the lottery."

Talk about flirting through text!

"Yeah, yeah," I wrote back, with the snarky hauteur of the online dater, "everyone thinks they're the lottery."

"Listen buster," my future date typed in, taking over the computer, "I'm the 20 million dollar lottery!"

I didn't realize she meant 20 million dollars - literally.

Knowing only that she's ballsy and funny, we meet. I walk into the Newsroom restaurant up on Robertson Blvd. and the waitress stops me at the front, "Are you with that woman there?"

I look over. She fits her friend's description. A raven-haired beauty. I nod.

"Lucky you," says the waitress, "She's a breath of fresh air!"

Like two teenagers who have recently been freed from prison (our marriages), we immediately fall into a kind of giddy passion. Signs of attraction flashing between us, full of laughter and shared pain and humor and stories about our kids.

We must be gazing wide-eyed at each other because later, some guy from the bar walks over with two glasses of water and says, "Here, you guys, drink this."

Tearing my eyes from hers, I look up and ask why.

"You're both on ecstasy, right?" he says.

We are, I suppose. But not the pill kind.

We're both fresh out of marriage and are tasting - for the first time in a long time - the liberation of being single and accepted and free. Then, I get an inkling that she's got a bit more dough than me when I say...

"So I'm thinking of taking my kids sailing this summer." I meant on like a 15 footer.

"Oh! I'm thinking of taking my kids out on our boat, too."

"You have your own boat? A sailboat?"

"Well, no. It's a 110 foot yacht. It's crazy. Right now it's in the Caribbean but we take it the Med for summers. "

Yeah, talk about a clue.

I drive to pick her up on our second date and the gates open to a two-acre spread at the top of Beverly Hills. It's been profiled in the Robb Report. I don't even know what that The Robb Report is yet, but I know a Rauschenberg on the wall when I see one. The Warhols. The tennis courts. Steinways. Leather floors in the study (Yes, that happens).

It turns out she's got an 18 million dollar estate, world-class art, a fully stocked 6 car garage and Skybox seats at Staples Center. Her "friend" who contacted me was her private clothes buyer (a job I didn't even know existed) who'd been visiting her mansion with a fresh load of couture and opened her online dating site to share how it's done.

I'm gobsmacked by the grandeur and taste of her 2 acre mansion. She gets into my Honda and we drive over to her friend's even bigger estate (replete with Picassos, Miros etc.) and Val Kilmer holding court by the fireplace. I play it as cool as I can, because I'm still struggling to make my mortgage while paying my ex wife's expenses at the same time.

I ask, casual as I can...

"So, I'm curious - how much is your nut for that house?"

"$65,000 a month," she says flatly.

"That's a lot of money," I sigh.

And she looks at me, serious and real.

"You know, it isn't," she says, matter-of-fact. "Look around the room. No one here is smarter than you. No one's more creative than you. And no one is more personable than you. If you made money-making a priority, you can do what everyone else in this room has done. You've just had other priorities. "

Clouds.

Parting.

Fast.

Really?

It's that simple?

In that one moment my life changed.

She had offered me an observation about possibility that I had never considered. Yes, I had made my writing, my "art" my priority. I had made raising my children and spending afternoons with them a priority. I had made learning and reading and crafting my mind and imagination a priority.

But I had not made money-making a high priority.

Her words stayed with me deep into the night. I had gone, in a matter of months, from a wife who literally told me "you just don't have money karma" when deal fell through or a movie didn't do well, to a woman who basically said that immense wealth was possible if I decided to concentrate on it.

Something genuinely shifted in me that moment. It was partly because I had a woman I respected offer faith in me, and it emboldened me. It was partly because I had simply never considered that this kind of wealth was a possibility for me. And it was partly because I could clearly see "Hey, people live this way. It's doable. And she says it's not that hard."

Within months, I was attending entrepreneur workshops. Within 2 years, my new businesses would generate half a million dollars on one very good weekend and five figures on many others.

Your life can change in a day. An entirely new direction can be inspired by one offhand comment you make.

As Dickens wrote in Great Expectations, "That was a memorable day to me, for it made great changes in me. But it is the same with any life. Imagine one selected day struck out of it, and think how different its course would have been."

Imagine how you can change the course of a friend or a man's life with but a phrase, and with the faith in their best self that you see.

Even if they don't see it yet.

Best Selling Author, Emmy-Nominated Producer, Screenwriter and Entrepreneur, Adam Gilad leads a community of over 80,000 men and women on their quest to create love and a bold, inspired life. Having served as a Stanford Humanities Center Graduate Research Fellow and host of National Lampoon Radio, Adam blends a bracing mix of research, humor and global wisdom traditions to help men and women break through the habits blocking their ability to open into love and freedom.

He's a regular contributor to Vixen Daily in the Personal Development and Inspiration section.