Navigating the dating game

Technology has revolutionized the dating world, but sometimes it’s better to go old school — especially if you’re on the older side yourself. 

Just ask Judith Gottesman, a former geriatric social worker who’s been running her matchmaking business, ” target=”_blank”>SawYouatSinai.com, said she sees a trend where older men tend to go for younger women. However, this scenario can have its own set of drawbacks. 

Older men “much prefer to use a home landline than a cell phone,” she said. “If there’s a 50-year-old man and he’s dating an age-appropriate woman, he’ll pick one night out of the week to sit down, listen to his answering machine, and call her back. If he’s dating a 30-year-old woman who’s texting and on her cell phone all day, she’ll say, ‘Why didn’t he call me all day? Why isn’t he texting?’ ”

Though the dating pool is more limited when singles over the age of 50 look for companions in their age groups, there is additional freedom when it comes to certain areas.

“When having children is not an element of marriage anymore, or you already have them or are not planning to have them, people aren’t hung up on the details they are hung up on when they’re in their 20s,” Salkin said. “Maybe you’ll look at someone with slightly different religious and family backgrounds.”

Those who use matchmakers to navigate the scene say it suddenly becomes much simpler. One Los Angeles resident named Jeff, who is in his 50s, utilized the assistance of Orly Hadida, aka Orly the Matchmaker, a Beverly Hills-based professional who’s been listed in the Guinness World Records as the most expensive matchmaker in the world. He said, “You don’t have to go to bars or do the pickup lines and everything else. She interviewed me, got my background information and did a lot of pre-screening. She tries to match you with somebody you’re looking for and vice versa.” 

Hadida, who is in her mid-50s herself, said that singles over 50 want camaraderie and monogamy, which is what Jeff (who requested that his full name not be used) was seeking.

“When you’re in your 20s and 30s you want to party and travel and don’t take things seriously,” he said. “When you’re in your 50s, you’ve been married and have kids and want companionship.”

Dee Gaines, who has a doctorate in neuropsychology and clinical psychology, and lives in Beverlywood, echoed those sentiments. She started 3InLove, a matchmaking service for older singles that incorporates the Torah and kabbalah’s marital values. 

Dee Gaines started 3InLove, a matchmaking service for older singles.

She said that as people age, they “go through the process of thinking about where they want to put their efforts for the rest of their lives. They ask themselves, ‘What do I want to accomplish with the certain limited time I have?’ They’re interested in settling with a partner they can share a routine with.”

Gottesman added that because health issues come up as they get older, individuals often look for partners who take care of themselves. 

“People want to find someone who is healthy because they lost a spouse who was unhealthy and they don’t want go through that again,” she said. 

Lifestyle compatibility over 50 is about more than health, though. It’s also about money and whether or not people are still up for adventure. 

“Some individuals don’t want a partner who can’t keep up with their lifestyle,” Gottesman said. “If they’re not retired, they want to be with someone who is also not retired. They want someone who has an active, productive life as well. That can be tricky because some people retire early and others never want to retire.”

In their 20s, singles are more flexible. They’re willing to modify how they function and negotiate on certain issues. Jenny Apple, who sets up Jewish couples throughout Southern California, said it’s not as easy to set up those over 50 “because they’re set in their way of life. It’s harder sometimes to get them to appreciate the value of being set up with another quality individual.”

Jenny Apple, California matchmaker

It’s not about being stubborn though. Apple, 31, from the Beverly Hills area, said it’s more about the baggage that comes along with being a certain age. 

“Sometimes it’s understandable. You have children or a sick parent to take care of, and you don’t want to uproot them. That’s a challenge, and a personal life decision, but people … have to weigh the factors,” she said. “They have to say, ‘Is it more important for me to have a partner in life or to be comfortable with my environment?’ ”

Aside from enlisting the help of a matchmaker and setting up an online dating profile, Gottesman recommends that singles who are 50-plus treat dating like they did at any age. That means getting out and mingling.

“If you just stay at home and don’t try to meet anybody, you’re not going to find that he or she will just knock on your door,” she said. “You should go to singles events or volunteer somewhere you care about.” 

Gaines and her partner at 3InLove, Trudy Green, are working on putting together singles events for the older population over the next six months. She said she continues to focus on people of this age for many reasons. 

“The 50-plus community is a wonderful population to work with,” she said. “There is such wisdom and knowledge that comes out of this group.”