This as-told-to essay is based on a conversation with Brandon Wade, co-CEO of Seeking. It has been edited for length and clarity.
When I met my wife, Dana, back in 2020, I wasn’t in a good place. I had just celebrated my 50th birthday alone. I’d already been married and divorced three times, which was quite painful. I no longer believed in love.
I was immediately attracted to Dana — with online dating, attraction is very important. The day after she messaged me, we talked on the phone for four hours. A few days later, I flew from my home in Vegas to Florida to meet her.
We discovered that — despite our 30-year age gap — we have similar values and upbringings. Dana is hugely ambitious and wasn’t afraid to ask me hard questions, like “What’s your biggest fear?”
Loneliness is my greatest fear. But when I met Dana, I realized it didn’t need to be my fate.
I felt left behind by dating sites
When I was a younger man, I felt left behind by the dating industry. I was successful and nerdy — an MIT grad. I’d focused so much on academics and success that my social skills suffered. Picking up women wasn’t something that came naturally to me.
I wanted to design a dating site that let men like me flex what we really have to offer: our competency, capability, success, and ambition. I launched Seeking Arrangements in 2006. We were clear about our intention to match younger women with successful men.
A lot of people thought this idea had a negative connotation. Most of the judgment was directed at the women. But women shouldn’t be judged for wanting more from life, and from who they’re dating. Wanting a generous, successful, ambitious partner isn’t a moral or ethical failing.
My parents have been married for nearly 60 years
In 2019, my company rebranded as Seeking and banned transactional dating. To me, transactional dating means setting concrete parameters, such as “If you give me X, I’ll do Y.” All relationships are transactional in some ways, but there shouldn’t be scorekeeping.
As Seeking, the company still aims to connect successful, ambitious people. Most of the women on our site are ages 18-35, while the men are ages 30-60. An age gap as big as mine and Dana’s is uncommon, though: the average age gap on our site is 12 years.
Seeking allows men like me to highlight what makes them attractive: their wealth, lifestyle, and accomplishments. In a sense, we’re more willing to explicitly say what’s often unsaid in dating: women value success in their partners.
My parents have been married for nearly 60 years. One of the things that attracted my mom to my dad back in Singapore was that he drove a car, not a motorbike. That showed her he could provide for the family she wanted to raise.
My in-laws are about 3 years older than I am
Today, Dana and I are co-CEOs of the company. She’s Gen Z, I’m Gen X, which gives us a good multi-generational perspective. In a way, we’re the biggest success story Seeking has had, and now we’re co-pilots in helping other couples find their match.
When Dana and I married in 2022, we didn’t get a prenup. I was a multimillionaire; Dana came from a middle-class family. We both wanted to show our family and friends that we were fully in this. There would be no fourth divorce for me.
Once Dana’s parents saw how playful and natural we are together, I think any doubts they had about us disappeared. I call her parents Mom and Dad, even though they’re only about three years older than I am.
Dana and I don’t have kids yet, but we want them. When our kids ask how we met, I’ll tell them it was a match made in heaven, but that it came with a lot of effort. The dating industry didn’t offer me a solution to find love, so I created one. I want my future children to know that if you’re willing to work hard and solve the problems before you, you can always have what you want.
