The idea of entering the dating world over age 50 might seem scary, but quite honestly, there’s never been a better time. Experts and senior citizens themselves agree that shifting social norms, increased social opportunities and better health care have all made life a happier and easier place for senior singles, and that’s especially true for those seeking new love. While challenges like health issues, finances, the practicalities of meeting people and blending families are certainly present, they’re by no means insurmountable — and the rewards of experiencing romance as a self-confident, independent and mature adult can’t be understated.

“I think your value system is certainly clear and in place,” says Rivona Levine, who began dating her husband George nearly 10 years ago, after the death of her first husband. “You know what characteristics you value and what you don’t value. I think you know yourself better and know what you’re interested in.

“You have a sense of knowing yourself, of confidence in yourself. It comes after a lot of years of living. When you’re a senior citizen you’ve gone through relationships of all kinds — that is, if you’ve exposed yourself and haven’t been provincial.”

How to Get Involved, and Why

Of course, getting back onto the dating scene as an older adult isn’t always easy. Licensed psychotherapist Tim Maggio explains, “A big issue is just trying to meet someone; making the connection can be a huge problem. At this stage in life there’s a risk of hooking up with someone who’s got a lot of baggage.”

Fortunately, attitudes about dating later in life are changing for the better. “There’s still ageism and the idea that people shouldn’t be dating after 50, but on the other hand more and more people are looking for a relationship so it does seem that things are looking up,” says Elayne Rapping, former professor of American studies at the University at Buffalo and author of several books on popular culture and social issues. “When you get older, no one wants to be alone.”

Rapping says she’s observed that factors such as improved health care for seniors and the trend of retiring later — continuing to work means not only financial independence but continued mental stimulation and motivation to be social and active — are facilitating a world more friendly to romance at all ages.

In addition to the workplace, there are multiple social settings ripe for making connections. Rapping suggests seniors start by looking to meet people “through family and friends or through church or synagogue [or social events for the nonreligious]. What you want is to find some decent, reliable person and maybe the best way to do that is through social connections.”

And meeting like-minded people is easier than ever now that more seniors than ever are going online: According to the Senior Citizen Journal, a study by the Pew Research Center’s Internet and American Life Project revealed that social networking use among Internet users ages 50 to 64 grew by 88 percent — from 25 percent to 47 percent — between 2009 and 2010. 

During the same period, use among those ages 65 and older grew 100 percent, from 13 to 26 percent. Maggio recommends “a reputable dating service that does bona fide psychological testing.” (Forbes rates eHarmony.com, PerfectMatch.com and JDate.com among the top sites.)

Alternatively, Maggio suggests getting involved in charity or volunteer work or political activism; this way, he says, you’re more likely to find “someone looking to give back, someone interested in making the world a better place.”

Overcoming Obstacles

The process of working up the nerve to get back on the market isn’t an easy one, but the single life can be lonely for seniors, particularly men of the baby boomer and WWII generation.

“Men who are widowed or divorced often do very badly,” says Rapping. “They’re more likely to have heart attacks or commit suicide. [Traditionally in these marriages], it’s the women who make the social arrangements and who run the household, while men are in the business world.”

Furthermore, she says, “Women are better at coping with emotional ups and downs,” as they’ve been taught to value close friendships and expressing feelings. Men, says Rapping, “don’t like to see themselves as vulnerable.”

That’s changing generationally, especially as men have become more active in the raising of children than in previous generations, but they still have trouble reaching out to peers, Rapping explains. “They’re willing to do more, but not necessarily to feel more.”

Rivona agrees that many differences are due to conditioning and societal roles. “I think women have more social relationships than men do,” she says. “I think men are often more limited in their relationships.

“Women have been socialized more to reach out to other people very often, though it depends on the woman and the psychodynamics of family and friends growing up. I think men perhaps aren’t reaching out to other people as women have been socialized do.”

More Equality

Rivona thinks this is changing thanks to more egalitarian marriages. “I think generations younger than I are more aware of equality and more equalness in relationships,” she says. “I can see in the generation my children’s age that men are reaching out more.

“I suspect their children will be more socially aware to reach out because there are fewer equality issues than in my generation, where you were kind of fixed in a certain role.”

Once you’ve met someone promising, there are certain challenges specific to seniors, says Maggio; with health issues and medications often come challenges with sexual intimacy. Maggio believes the answer is to “accept intimacy in terms of its true meaning. So many people connect it with sex and they’re two different things; it’s important to not have unrealistic expectations.”

At the same time, advances in medicine have improved the sex lives of millions of seniors, so it’s worth talking with a doctor about options for addressing sexual problems. Financial issues can also be a concern, especially when remarriage is on the table.

As Maggio points out, “If one remarries, that may affect someone’s pension or retirement plan; to get legally married might stop those things.” Maggio recommends looking at these consequences pragmatically, and suggests, “If legally marrying is going to cause issues, just move in together!”

Blending Families

Finally, when adult children are involved, introducing everyone may be tricky ground. Whether the relationship is headed for marriage or just for fun and companionship, it’s not always easy for children to accept the idea of their parent with someone new.

Maggio advises, “Put everything out on the table. Adult children can understand that we can love more than one person in our lives. Just because one relationship has ended doesn’t mean that person wants or needs to spend their life alone.”

Rivona and George Levine experienced this firsthand, as they both have adult children. “When there’s a remarriage or a serious relationship and there are adult children involved you have to be aware that the psychodynamics of each family may be different than what you had,” Rivona says.

“I have two married children, he has two married children and the psychodynamics of that can be easy or difficult depending upon how they choose to view this relationship, and how they choose to interact or not interact with a relationship and with the adult children of the other spouse or other person.”

She says the key, as always, is communication. “I think that the adult children have to see what this relationship is, why it is, and think about that and be understanding.”

Loving Someone New

George and Rivona Levine had known each other for some time before George’s wife passed away. They connected afterward and dated for two years before tying the knot. “We went out for dinner, we went to concerts, to movies; we did things any age group would do that are not constricted by young children,” says Rivona.

For the Levines, the decision to remarry was a natural one based on positive past experiences. George “came from a good marriage and liked being married,” and Rivona says, “I had a very good relationship with my first husband; I like the companionship of marriage, the security of a person that I respected and admired and loved.”

Rivona explains that she and George were an equally good fit: “Our value systems were quite similar and compatible.”

Even in the happiest of blossoming relationships, perhaps one of the most important unseen challenges is the simple task of learning how to be with someone new, whether you’re dating again after a long marriage or getting out into the dating scene after a hiatus.

“As you age you get fixed in your ways and after a very long marriage, which mine was, I didn’t think about what I was doing and how I was doing it,” says Rivona. “In a different relationship with a different person who comes with his or her own set of ways of doing things and thinking about things, it’s an adjustment.”

To overcome this without putting too much pressure on a new romance, Rivona advises senior singles to start small. “If you’re going into it for companionship, look for friendship. If you’re a senior citizen, hopefully you know what you need and how you need it, and you can remember to be aware that other people also are in that situation.”

Taking that first step to begin dating is a leap of faith, to be sure — but it’s one that can bring profound joy and improved quality of life, and thanks to a smarter society, better medicine, better technology and the gifts of maturity and wisdom that advanced age brings, the chances of success are better than ever.