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."
Dating online the second time around - after divorce or the death of a spouse - isn't always second nature for the nation's 78 million boomers, let alone people who are 65 and older, but neither is it all that scary.
Yet they often have unrealistic notions of how to hunt for love and companionship, said Pepper Schwartz, a sociology professor at the University of Washington in Seattle, sex and relationship expert for the AARP, and developer of an algorithm to make matches more meaningful on the dating site PerfectMatch.com.
"People 65 or older, they're picky in a different way," she said. "Young people tend to go for looks, period. Older people often have a little bit more leeway on what somebody looks like, but then they have all these other kinds of requirements that may or may not be realistic."
For example, a snowbird with a second home may be looking for a mate willing to winter in Arizona. Others may unnecessarily limit possibilities by ruling out partners with all health issues.
In addition, Schwartz said, "Men are very interested in women being self-sufficient. Women are deathly afraid of becoming nursemaids, but long lists can really hurt. I hate the word settle, but you need to be practical."
Schwartz said most are looking for a long-term relationship within five years of their own age.
