June 2026- Save $7

How It Really Started

My name is Jay, and I started WeekendDating.com on February 14, 2003. Valentine's Day.

At the time, I was single, going through a difficult period, and feeling like too much of life was passing me by. Weekends were especially hard. Friends were pairing off, people were moving forward, and I felt like I needed to make a real change.

WeekendDating was not created because I sat down and said, "Let me build a dating company." It started because I needed a way to get myself back out into the world. I wanted real faces, real conversations, and a place where singles could meet in person instead of sitting home wondering what might have been.

From A Personal Lifeline To A Real Business

During the day, I still had my corporate job. I had the suit, the title, the steady paycheck, and what looked like security from the outside.

But inside, I wanted more. I wanted to build something that felt like mine. Something honest. Something that helped people. Something that gave me a reason to walk through the door and keep going.

Then came a turning point at work. My role changed, my pay was cut, and the thing I thought was safe suddenly did not feel so safe anymore. At first, it felt like a setback. Looking back, it may have been one of the biggest pushes of my life.

I slowly cut back from five days a week, to four, then three, then two, then eventually one day a week, while WeekendDating continued to grow.

And when that corporate chapter finally ended, something unexpected happened. The thing I had feared for years actually gave me freedom.

What Grew From It

Since 2003, WeekendDating has hosted speed dating events, singles mixers, virtual events, activity-based events, and social gatherings throughout New York City, Long Island, Westchester, Connecticut, and other areas.

But the part that means the most to me is not just the number of events. It is the people.

Over the years, couples have met through WeekendDating, gotten married, and started families. What began from one lonely chapter turned into something that helped create real relationships, real marriages, and even children who are here because two people met at an event.