Sherry Alpert never watches a movie twice. But this winter she made an exception to her rule: She headed back to the theater for a second viewing of "Something's Gotta Give," Hollywood's valentine to mature love. As a 50-ish public relations consultant who has been divorced for five years, she knows well the foibles, frustrations, and poignant humor of midlife dating, as played out on the screen by Diane Keaton and Jack Nicholson.
"It's nice they finally made a romantic comedy for people over 50 who are getting a second chance at love," says Ms. Alpert of Canton, Mass. "You get so tired of those older man-younger woman movies."
After years of remaining largely in the shadows, midlife daters are getting their day in the sun. In addition to the Keaton-Nicholson romp, a play called "Bad Dates," about a 40-ish divorcée who is reentering the dating game, just ended a successful run in Boston.
Even dating services and websites are beginning to target older clients. In Denver, a new matchmaking service, Classic Connections, caters specifically to the 50-and-over set. While younger singles want to marry and have a family, those in their 50s and beyond are typically more interested in long-term companionship, says founder Kris Kenny.
"A lot are getting close to retirement, they've put away money, and they want to explore the world," Ms. Kenny says. "They would just love to do it with someone else."
Never have so many Americans been unattached in their middle years. The 36 million singles over 45 account for nearly 40 percent of that age group. Fifteen percent of Americans in their 50s are divorced, 4 percent are widowed, and 6 percent have never said "I do."
For moviegoers watching Nicholson lose his heart to Keaton after first being smitten by her under-30 daughter, "Something's Gotta Give" raises an intriguing question: Are middle-aged men in real life choosing women who are their contemporaries? Or is it still true, as Keaton observes early in the film, that "the over-50 dating scene is geared to leaving women out"?
Opinions are decidedly mixed.
"The vast majority of men still prefer younger mates," says April Masini, a relationship expert in Beverly Hills, Calif. Nicholson himself has reportedly been spotted with a 30-something girlfriend.
But Patti Feinstein, a dating coach in Chicago, thinks it's a misconception that men want to date young women. "Many complain that they just can't relate intellectually to a woman who is significantly younger," she says. "They don't want to go dancing in a club."
What they do want is women who are active.
Scott Wheeler, who owns a multimedia development company in Chicago, prefers the company of women his age.
"That's really worked in my favor, because a lot of men my age want someone who's 15 years younger," he says. "They're totally missing the boat in all respects."
Six months ago Mr. Wheeler began dating Emily Calvo, a freelance writer he met online. She is three years older than he is. An AARP survey last year found that a third of women over 40 are dating younger men.
"In general, the more mature the man, the more willing he is to date women his own age," says Mary Valentis, who teaches popular culture at the State University of New York at Albany. "He doesn't need a trophy girl to make him feel good."
Still, both sexes harbor stereotypes about age. "If I say a woman is 58, men think she's sitting in a rocking chair, knitting," Ms. Feinstein says. "When you say 55, they associate it with an old lady. It's just not true." Similarly, women are likely to regard men in their age bracket as couch potatoes.
Michael Lasky, coauthor of "Online Dating for Dummies," calculates that in terms of social experience, a generation is about seven years. After that, a couple's tastes in music, food, and entertainment, along with their points of reference, vary widely. "Once you start going beyond 10 years, you are adding one more complication to the challenge of mating," he says.
Beyond the question of age, many midlife daters must confront that dreaded word "baggage," a reference to spouses and offspring from previous relationships. Speaking of "the children situation," Alpert says, "I've met men with 6-year-olds and men with 39-year-olds, men who are single who still want kids, and twice-divorced men with two sets of kids. If they've still got young kids or teenagers, they want someone who's OK with that lifestyle. I've paid my dues with teenagers."
She's also parlayed these dating adventures and misadventures into a script for an as-yet-unproduced play, "Single Again and Hating It."
To newly minted singles coming out of long marriages, the prospect of dating can be daunting.
"They just don't know where to turn, especially if their friends are still married," says Kenny, who runs the over-50 matchmaking service. "They don't know what to wear, how to act on a date, or who pays for the bill." About 70 percent of her male clients pay on the first date.
Wheeler, who usually takes a first date to dinner in a restaurant, finds that some women like a man to pick up the check, while others prefer to split it. "Some people say that if she pays her own way, she doesn't like you," he notes wryly.
Then there's the confusion wrought by changing sexual mores. When those in their mid-50s and beyond were dating the first time around, the biggest romantic question was whether to kiss on the first date. "That was when it was easy, right?" Kenny says with a laugh. She urges clients to get to really know a date before becoming romantically involved.
When Richard Nosbisch of Denver was widowed 2-1/2 years ago after 22 years of marriage, friends had to nudge him to start circulating. A six-month membership in a dating service proved to be "not useful." He also shuns computer dating. As public relations director for the Art Institute of Colorado, he prefers to meet women through friends or community activities, where people have common interests.
Decades ago, when lyricist Sammy Cahn wrote, "Love is lovelier the second time around," singles didn't need such 21st-century skills as writing personal ads or cruising websites, where some date-seekers practice what Mr. Lasky calls "age deflation, weight deflation, and picture fraud." Translation: They lie about their age and weight, and post fuzzy or outdated photos.
Alpert tells her own blurry-picture stories: "One guy, when I met him, had a very cheap toupee. Nothing turns me off more than a toupee. Another one was much heavier, and his hair was dyed."
Onward to the next suitor.
Yet some midlife singles, like their younger counterparts, praise dating websites. Lasky, for one, met his fiancée online.
Kenny encourages singles to go to activities that interest them. Group events offer a low-key way to meet, without the awkwardness of a date. "Find out what makes you happy," she says. "When you're dating, you can look for someone who complements those things."
However couples meet, dates who get too serious too fast rank among the top complaints of single men and women in their 50s, according to the AARP survey.
For a woman interested in dating, Professor Valentis says, the challenge is to like herself at any age and accept her evolution as a person.
"That doesn't mean neglecting her looks," she notes. "Good looks in mid-life come from a sense of self-confidence, self-love, energy, and humor. Diane Keaton was so appealing because she was not shallow. She had depth, confidence, and was very strong."
Despite the challenges, midlife dating can have rewards. Ms. Calvo, the author of "25 Words or Less," a guide to writing personal ads, finds that as an empty nester, she can be more serious about a relationship because she has more time to devote to it.
As Valentine's Day approaches and romance fills the air, singles with silver threads among the gold can take encouragement from Kenny.
"It's never too late to make new memories," she says, quoting the slogan for her matchmaking service. "You could be in your 70s and 80s and still fall in love."
Those who are weary - or leery - of the dating scene can also take a cue from Nicholson, who tells Keaton in the movie, "You can't hide from love for the rest of your life just because it might not work out."
Wheeler offers advice from his experience: "Remain calm, and just keep going. You want to try to be professional in the search. You have to be just really patient."