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Since separating from her husband, one Boston-area alumna in her late forties has had numerous dates and even a long-term relationship. “But it’s oddly difficult to meet people,” she says. “I’ve done on-line dating, matchmakers—the gamut. I did see someone I liked while jogging in the woods, but I didn’t get his number. That old adage ‘Do what you like to do and you’ll find someone you like’ doesn’t really work anymore.” 

For those over 45, the world of dating is more complicated for a variety of reasons, ranging from the logistical to the emotional. For many, returning to that scene after divorce or the death of a spouse means adapting to new modes of social networking, such as Internet dating sites. For others, “putting yourself out there” requires gearing up emotionally and physically after a long hiatus—or being more open about who “the right” person might be. For everyone older—and less energetic—facing the risk of rejection takes courage, creativity, and resilience: in short, more personal effort.

“After age 45, single people face a fork in the road,” says Rachel Greenwald, Ed.M. ’87, M.B.A. ’93, a dating coach based in Denver and the author of Find a Husband after 35 (Using What I Learned at Harvard Business School). “Either they decide they are happy with their life the way it is, and take the chance that Mr. or Ms. Right will land on the doorstep serendipitously,” or they grow outside their comfort zone—asking “coworkers, your Realtor, your stock broker, your neighbors, and other people you barely know to fix you up with people, going on speed dates and lunch dates…it can feel embarrassing,” Greenwald continues. “But I see it as empowering—to take things into your own hands and be active. That is how the game is played after 45.”

Geordie Hall ’64, for example, divorced after a 30-year marriage, now lives in rural Vermont and meets women through outdoor activities, volunteering, or community fundraisers. “I’m very active: I go hiking out West, backpacking, and I’m a passionate skier,” he says. “It’s important to me to have somebody who shares some of my lifestyle, so I meet people through activities I like. My objective is not to be alone the rest of my life. Sharing experiences on a daily basis is very important to me.”

 


An AARP report published in 2003, Lifestyles, Dating, and Romance: A Study of Midlife Singles, found that what respondents liked most about being single was “personal freedom”; the worst aspect was “not having someone around with whom to do things.” Older daters seem particularly torn between these two desires, and each side tends to be more “set in their ways,” says matchmaker Sandy Sternbach, owner of The Right Time Consultants, who specializes in clients who are 36 to 70. “But mature love is really about caring for someone else’s well-being,” she counsels. “It’s about putting up with people’s imperfections, their struggles—sometimes illnesses—and knowing who they are and helping them have a good life with you. It’s not all about you.”

The AARP report also revealed what seems a more general ambivalence about dating. Though 63 percent of respondents were either in exclusive dating relationships or dated regularly, the balance of midlife singles were either “interested daters” (not dating, but would like to find a date), “daters-in-waiting” (not actively looking, but would date if the “right person came along”), and “disinterested” non-daters.

Overall, men were slightly more likely to date than women, but women in their forties went out more often than their older counterparts. On dates, both men and women sought a “pleasing personality” and common interests and values. Women tended to add financial stability; men more often noted physical attractiveness and potential for sexual activity.

“For many guys, how the date ends is the biggest thing on their minds throughout the entire date,” says Manhattan-based love-life coach Nancy Slotnick ’89, who describes herself as somewhere between a matchmaker and therapist. “This is also important to many women. People want to know if there is romantic potential or not.” But the author of Turn Your Cablight On: Get Your Dream Man in Six Months or Less and owner of Cablight.com acknowledges that questions that take you back to high school—Does he/she like me? Should we kiss at the end of the first date?—can feel especially awkward or silly for older people who have lived through more serious life experiences.

Divorcée Sarah McVity Cortes ’83 says she makes her interest clear in other ways—saying she likes her date, suggesting a second meeting. “But I’m not going to kiss anyone I don’t want to kiss,” she says. “If women start down that slope of orienting themselves to make the man feel comfortable, where does it end?”

Slotnick says her more proactive clients aim for a date a week. “Fewer than that, and you’re not dating enough to work the numbers and to become a little more numb to the rejection factor,” she adds. “People who date often come to realize that it’s not about being ‘undatable,’ it’s about seeing if two pieces of a puzzle fit together.”


Boston attorney Jeanne Demers ’83, a former biological anthropology concentrator, has “no doubt we are wired in certain ways physiologically to be attracted to certain people,” but adds, “Of course, we also need the emotional tools to effectuate it in a healthy way.” She has twice been close to marriage, but broke up with her last long-term boyfriend in 2007. “I guess I’m sort of half-hearted about dating,” she says. “It takes effort and sometimes I’m not willing to work at it.” She says unmarried men her age seem to have problems with core identity—they lack professional focus or emotional maturity, or are unable/unwilling to commit to a relationship. “Divorced men and older men are easier to connect with.”

 

If you can find them. Those returning to “play the field” will find the “field” has moved—and shrunk. “Now, most of your friends are married and get together for dinner parties in the suburbs with other couples,” says Rachel Greenwald. Those still at the peak of their careers (ages 45 to 65) probably work a lot and tend to be more isolated because they are bosses in a corner office, or work from home. Most older singles are also divorced with children, she adds, with little free time outside of solo parenting and career obligations.

With those over age 65, generalizing about dating trends is hard, cautions psychologist Judah Ronch, a professor at the University of Maryland–Baltimore County, who specializes in geriatric mental health. But overall, he says, such singles are more conservative (they don’t trust the Internet as a social forum) and they tend to date people they already know: past loves, family friends, or old acquaintances who are now divorced or widowed. “Often, by then, all the static that comes with relationships in your twenties has been taken out, and a relationship can flourish,” Ronch says. “They know they don’t have time to waste, and they are looking for comfort, companionship, closeness”—and, often, sex. Acceptance of others’ foibles and frailties is also a part of what makes these unions successful.

 

Increasingly, those 45 to 55 are meeting online, through sites like Match.com, eHarmony, and Yahoo Personals. (There are also many shared-interest niche sites that focus on ethnicity, race, sexual orientation, religion, or activities.) Those over age 45 comprise the fastest-growing segment of users at Perfectmatch.com (it has five million members and a subsection for baby boomers), and at PlentyOfFish.com, where they tend to log on and stay on more often than younger users, says CEO Markus Frind: “They are more committed to the dating process and have a goal in mind. They don’t want to be alone.”

The Boston-area alumna who has used Match.com and Jdate.com (for Jewish singles) says she hates the process because it’s impersonal, impolite, and superficial. Perusing the photographs and bios of men “takes on a video-game quality—you can look at 40 people a night and take a pass on all of them,” she says. “And because you have so little to go on, you gravitate toward the most attractive photos and make snap decisions based on that.”

Greenwald has conducted hundreds of interviews with single men for her forthcoming book Why He Didn’t Call You Back. She says the Internet “candy store” mentality often leads to a paradox of choice: “After 45, all of a sudden, the guys who couldn’t get any girls in high school have so many wonderful women coming across their paths, they become paralyzed, sadly, because they are looking for perfection—which doesn’t exist.” Typically, she says, a man may be dating a “beautiful, intelligent, warm woman, but she doesn’t like golf. He says, ‘I don’t know if I can live with someone who doesn’t like golf.’ It is so ludicrous. I want to say, ‘Go get a golf buddy. Why should your wife have to play golf?’”

Setting prerequisites about the “right person” is the wrong approach, says Dawn Touchings, president of The Right Stuff, a 5,000-member “introduction network” based in New Jersey that caters to Ivy Leaguers and alumni from other top schools. Database matching, used by many Internet dating sites, relies on input from candidates who list their preferences: tall/successful/athletic/religious/likes animals/loves sunsets…. “What I’ve found is just the opposite,” Touchings says. “Many of the people who meet on our site tell me the person they are compatible with did not fit any of the categories they set.”

Both Greenwald and Sternbach concur. Sternbach often omits last names when introducing people, to avoid any pre-date Google research. “Clients end up using the data to exclude people,” she explains. “They never allow themselves the chance to slowly unfold with another person. That kind of vulnerability is something a lot of highly successful professional people are not comfortable with. But it’s also part of the mystery and excitement of two people coming together.”

How people evaluate partners and their own needs necessarily changes over time, Greenwald says. Those in their twenties and thirties look at potential—to hold down a job, earn money, be a good parent, evolve. But people in their forties through their eighties, she explains, are fully formed: they can be stuck in a career rut because of financial considerations (alimony, child support, pensions, mortgage); have health problems; or have emotional “baggage” from prior life experiences, which is entirely normal. “You have to evaluate people as a known quantity and accept who they are now,” she says. “It’s a very different view, and I don’t think that people later in life [are aware enough to] make that important switch.”

As Demers puts it, “I’m more set in my ways now.” She wants to meet a compatible man, but is “not unhappy; I like my life.” Someone she now dates casually is unlike any of her previous partners—he’s Jewish, nurturing, has a sense of humor, and thinks Demers is funny. For a while there was some potential. “Unfortunately,” she says, “the ‘chemistry’ is missing, which makes me wonder: is my wanting to be in a romantic relationship with a man who is my ‘best friend’ an unrealistic expectation? Why can’t both aspects be in one man? Of course, it’s me too. Obviously, I have my own baggage. But at least I know it—and I’m working on it.”

In the end, emotional obstacles can often be worked through, says Sternbach. She points to a client in her seventies who finally met a man who “makes her laugh; they travel together and they are simpatico. My client has never been happier. You can have that—be in love in your seventies—but it’s something you have to work at, something that has to be nurtured.”