At 57, after a decade of pushing profiles and awkward meet-ups with strangers, he's married to 54-year-old year Debbie, a former Marine he met online two years ago.
"I had plenty of lemons before lemonade, believe me," said Valentino, a furniture salesman in Long Branch, N.J.
One prospect said he was too old. Another went out with him to win a bet with a co-worker. A third told him all about her two grown sons and "their careers in the penal system, only they weren't guards."
That's when Valentino ventured onto a site that caters to older people -- at the time called SeniorPeopleMeet.com. He quickly let go of his prejudice against the word "senior" and found Debbie, who has war stories of her own about trying to find a mate her age online.
"On other sites, most of the men who would contact me were a lot younger," she said. "I would say why are you writing me, I'm looking for somebody my own age. I made it very clear in my profile. They would say I want the experience of dating an older woman."
On eHarmony.com, an industry leader, people 50 and older are one of the fastest growing segments among its more than 33 million users worldwide. The same goes for competitor Match.com, which said about 25 percent of its members are between 50 and 65. Boomers on Match have grown 89 percent in the last five years, site officials said.