The Remarriage Game

By staff February 1, 2008

Prince Charles finally did it. Rudy Giuliani did it. Elizabeth Taylor did it seven times. Perhaps you, your neighbor or your parents have done it, too. I’m talking about getting remarried. Love can be lovelier the second (or third) time around. And no one knows it better than those of us here in beautiful Sarasota, arguably the remarriage capital of the world.

But how do you find the person who is going to be the love of the rest of your life?

The good news: you’re in the right place. Last year Fortune magazine named Sarasota as the best place for singles over 55. The article, “Where to Retire in Style,” told the nation that with all its cultural amenities, Sarasota is the perfect place for well-off retirees to meet, listing as a bonus “countless activities and clubs geared toward singles and organized around interests from wine tasting to ballroom dancing.”

But the tried and true rule still applies: Meeting through a mutual friend still ranks as the No. 1 path to successful pairings. Why? Perhaps our friends know us better than we know ourselves.

Luckily, many women in Sarasota love to play matchmaker. One of those, Deb Knowles, boasts numerous triumphs and only one flop: “She married him too soon,” Deb explains.

That’s how this petite, energetic, 50-ish brunette met her husband, Charles, 10 years ago. She was new to Sarasota when at a black-tie function, “My friend Higgins walked across the ballroom with Charles, put our two hands together, and said, ‘You two have got to get to know each other.’ We’ve been together ever since,” Deb recounts. Charles was 52 at the time, with two grown children. His wife had died nine months earlier, and this was the first time he was out at an event. Now Deb sees her own talent for matchmaking as a gift. “I owe it to the universe,” she says.

The most important thing to remember, Deb explains, is to keep a positive spin on the dreaded dating process. “I tell people, ‘You might have to meet 100 people before you meet the right one. So if you have a bad date, just think, ‘OK, that’s one less person I have to meet before I find Mr. Right.’ Meet at Starbucks and have a coffee. If you like each other, great; if you don’t, say goodbye. It’s only coffee,” she says.

Her greatest hit? “Julian Parry and Emily Walsh,” she says happily. Julian is a young globe-trotting businessman and Emily is the editor and photographer for the Black Tie section of her family’s Longboat Observer newspaper. Their marriage last year was one of Sarasota’s most high-profile events. Julian lived on Deb’s street. Once, when he went away on a business trip, he brought Deb’s dog a gift. “It just won my heart because he is such a dear person,” she says. She didn’t know Julian’s phone number, so she left him a note in his mailbox: Call me, I have someone you have to meet. “I told him that she was fabulous and I gave him her phone number.”

But Emily, she discovered, had already met Julian while taking photos at a Halloween party where he was dressed as a slice of pizza with a pepperoni on his head. “‘The pizza guy?’” Deb remembers Emily asking. “‘You want to fix me up with the pizza guy?’ But they went out and they’ve been together ever since.”

An old friend of mine, a widow who was reluctant to meet anyone, has a new man in her life, thanks to a persistent friend. “I’m never sharing my bed again, and I am certainly not sharing my closet,” she’d told me along ago. She had a very full life, but she felt there was something missing—intimacy. Then a mutual friend actually brought the man, whom she thought was perfect for her friend, to her house so they could meet each other. The three spent the afternoon schmoozing. The pair has been together for a while now and are having the best time. “Both are more the quiet, stay-at-home type. They’ve done all the partying and they are over it,” the friend says of the couple.

Two days after hearing this story, while waiting for my take-out order at Captain Brian’s restaurant one evening, I spotted the two lovebirds in question—necking at the register while waiting for their change. They couldn’t keep their hands off each other, and they are in their very late 60s. They turned and saw me. “This is my new boyfriend,” my old friend said, offering no apologies.

Fortunately, Sarasota is a very social community, and since a person’s family often isn’t here, this leaves him or her open to social relationships, unlike so many places up North where Sunday dinner with the family is required. But you’re more likely to find the right new relationship if you have a goal and understand what you have to do to get there. I always tell people that by approaching their relationship search with the same clear-headedness and logic they use in other areas of their life, they can and will make this happen. It’s also a good idea to be in your best possible shape mentally and physically as you begin the process. Now is the time to lose the extra 10 pounds and to start a regular workout program.

And remember to keep a positive attitude. I have a friend who always seems to be enjoying herself at events, no matter if she is with an escort or solo. Men love Claire (not her real name). At 53 she is successful, very attractive, never married, but a survivor of several long-term relationships. There’s no shortage of suitors, but she prefers the single life—at least at this time. Her advice: “Enjoy life and smile a lot and be comfortable with yourself. You meet people no matter where you are, in the produce department of the grocery store, or walking down the street. The desperation tango doesn’t work. People sense it. It has to be real; you can’t pretend you’re smiling.”

And don’t despair if you have some years to your credit. Clichés notwithstanding, “I don’t think [all men] necessarily want a younger woman,” says one 60-ish widow. “When people reach their 50s, 60s and 70s, they tend to be more relaxed. I find men better at that age. The man you meet today with kids gone and business under control might not be the man you would have fallen for 10 years ago. They have more time to be a better companion and to appreciate the time you have together.”

Still, you must face facts. Many men are attracted to younger women, and it’s interesting to hear why. Several of the people I interviewed said men were sometimes intimidated by women their own age. With a younger woman they feel like they can be in charge. “I don’t think they necessarily want a younger woman,” says one 60-something divorcee. “But when a man in his 80s loses his wife of 50 years, he is not attracted to a woman of the same age. Most likely he never saw his wife realistically at the age she was. And that is a lovely thing.”

And make sure you’re looking for who’s right for your 50-year-old self, not your 30-year-old self. The great anthropologist Margaret Mead, in her classic study about the sexes, Male and Female, suggested that changing partners in life is entirely appropriate: “A world in which people may reorient their whole lives at 40 or 50 is a world in which marriage for life becomes much more difficult.” The suitable reproductive partner may not be the traveling companion, golf partner, or intellectual counterpart who will fill your needs down the road.

Expect to face plenty of competition along the way—especially if you’re a woman looking for a man. At the Sanderling Club, where I used to live, when a beloved wife passed away, the widowed and divorced women would line up with provisions the next day. The “Casserole Brigade” was ever-present in death, and it provided a comfort factor for the newly widowed man—and an opportunity for the single women. I did not observe any casseroles being delivered when a husband died.

I know a woman who has met two husbands from reading the obituary column. She called with a sympathetic ear, offered to meet for a “support” cocktail, then dinner—and before the year was out, the knot was tied.

One prominent Sarasota gentleman in his 80s recently lost his wife of 55 years. A friend approached him after the funeral service and suggested he might enjoy the company of a woman who herself had recently lost her husband. I was shocked and questioned her protocol. “Why waste time?” she shot back. “After all, it’s not like she’s coming back, and let’s face it, he’s not getting any younger.”

Taking up an athletic activity is a great way to meet in Sarasota. Matt (retired dentist) and Connie (successful real estate broker) met at an Adidas running camp at the Sarasota High School track. A friend in New York told Matt to look up Connie when he moved to Sarasota, as she had a lot of the same interests as he. They started running together as partners, became good friends and then got married.

Another couple used to run every morning, going in opposite directions. Finally, one morning Jim crossed the street and said, “We pass each other every day. At least let’s say hello and get to know each other.” Now they’re married. The moral of this story? Be bold and friendly.

And don’t write off Internet dating as just for college students. It can work very well for older people, because it allows you to be very specific about what you are looking for. There are sites for Italian singles, Jewish singles—just about anything you would want. You can see what the person looks like and correspond before meeting. According to Kathryn, age 62, twice divorced, “The Internet is what almost all my single women friends end up using. But if you don’t look good or have good photos, it’s very hard. So it’s terribly important to stay in shape and stay up-to-date in hairstyle and fashion. A surprising numbers of women over 50 come across as too matronly, and often as boring. What’s called on some of the Internet services ‘a few extra pounds’ is a real turn-off for many men, even though a lot of the men we meet have plenty of those extra pounds themselves.”

I love the tale of the 60-year-old Sarasota woman who on a dare placed an ad in the Harvard Review. She was explicit about what she was looking for and candid about herself. She sorted through the responses and found one she liked, but he lived in Alaska. They wrote and e-mailed each over a period of six months before they met. He was about to retire and happy to make the physical move to a warmer climate.

Even the personal ads in the newspaper can pay off. Marilyn, at age 70, was a smart, good-looking, upscale divorcée of 30 years. The mother of five grown children and a volunteer at Van Wezel, she had her dog and a full life. She had never dated and never wanted to. One day she spotted a personal ad in the bottom corner of the local paper and said to her daughter, “I should write to that man because no one will see his ad.” She mailed him a response. Two days passed and he called. They made a date for lunch. They had such a wonderful time that they spent the entire afternoon together, and then it was six o’clock. They had dinner together and Marilyn said to Herman (nicknamed Hi), “Well, I guess I’d better go home now.” He said, “Why? No one’s there.” So she stayed over and they have been together ever since. That was four years ago.

And make sure you go to all your high school and college reunions. The success rate is amazing. John and Mary grew up in Philadelphia. He, a dashing bachelor at 42, had never married. She was an established musician and a recent widow with two children. They had gone to grade school together and re-met at a school reunion. On their first date, up North, he said, “I have a condo in Sarasota.” Many dates later, when Mary came to visit, John took her to Marina Jack for lunch and to The Summerhouse for dinner. When they returned from dinner, he gave her a ring and proposed.

Where you won’t find him: The bar scene. Whatever you do, do not go to “Happy Hour” at any of the local watering holes. You’ll be competing with physically enhanced and considerably younger women.

“Trolling at the upscale bars is not going to provide you with a meaningful relationship,” says someone who has worked at several of Sarasota’s most popular nightspots. “I’ve seen it all, and most of these guys are out with a purpose—and it’s not commitment. Usually, they’re looking for arm candy.”

My husband and I stopped at the Ritz bar one evening, having heard they have great bands. I was positively frightened by what I saw. There they were: not-so-hot grandmas, the women in their 70s and 80s, many dressed in skintight pants, spike-heeled shoes, bare midriffs and hair that does not move. You can be beautiful at every age, but dressing like 17 at 70 really doesn’t work.

Vanessa, age 67, a very youthful and attractive architect who is not looking for a husband but enjoys the companionship of men, has a better alternative: “Go have a latte at Borders or Barnes & Noble. Or have dinner at the counter at an upscale restaurant—not at a table,” she says. “Often a conversation will start up with some guy sitting there eating—not just drinking.”

Of course, once you’ve found someone who interests you, you may also find some hurdles peculiar to the later-in-life relationship. Sex, or the lack thereof, is the biggest problem women report in mature relationships. As one 60-ish woman said, “He can’t perform.”

Veronica, a 65-year old attorney, says, “Some older men, especially those who have been in one long marriage, are—to put it bluntly—lousy lovers. They often have no idea about how to please a woman—just themselves. I suppose they could learn, but that’s a difficult job. Some men take Viagra, I guess; some use other methods; and some simply don’t acknowledge that there is a problem. It becomes more and more common as you date older men.”

Another problem that can (ahem) arise relates to that other perennial bugaboo, money. “You have money, he may or may not have as much money, or something similar,” says Claire, 53. “A man who has been divorced several times has taken some big financial hits, particularly if he has children.”

Joan, 64, comments, “Many men in their 50s or 60s, even those with upscale careers or professions, have been damaged financially. They may be paying large alimonies or supporting kids through college. Some have lost pensions or jobs. It’s amazing how many are living in somewhat reduced situations—and you wouldn’t suspect it at first meeting. They talk about the delights of ‘downsizing.’”

Amanda, 57, says she always offers to split a bill. “But many of my women friends think the man should always be the one to pick up a bill,” she adds. “This, in my opinion, is a holdover of old attitudes on the women’s part. Many upscale women in their 50s and 60s have not had working careers or incomes, and they are used to being taken care of. Many men at the same age are no longer interested in ‘taking care’ of a woman—at least, they don’t want to enter into a relationship with someone who seems to be expecting them to foot the bill for everything.”

And then there’s the issue of the needy, or walking wounded. Dot, 55, sums up this one: “Some men, after long marriages, are rather helpless on their own. I’ve sometimes felt like I was being interviewed for a job rather than getting to know a new man. If they’re retired and newly single, some are at a total loss as to how to fill their lives. They’re not passionate about much of anything. How interesting is it to spend time with a guy who just plays golf?”

Finally, there are extended families. Grown or nearly grown children can be tricky to deal with. One woman told me, “Sometimes the children are so angry over their dad’s divorce, or sad over the death of their mother, that they don’t want you in their dad’s life. Other times, the man’s grown children are beset with problems of their own—drugs, drinking, school dropouts. These situations, while understandable and sad, can consume a lot of the man’s time and attention—and money—and have the potential for getting in the way of a relationship.”

But why focus on possible negatives? We know one thing for certain: Love can happen anywhere, when we least expect it. By the time we have matured, we know what we want and need. And most men and women are looking for the same things: love, companionship, and sexual fulfillment—the right person at the right time. So take charge of your life and go after what you want. As the song from Casablanca says: “Woman needs man, and man must have his mate; that no one can deny. The fundamental things apply as time goes by.”

Susan Curtin Kelley was a divorced, single mother of two for a long time, living in Boston, when she was introduced to William Kelley by her best friend, who was married to his best friend from college. The two have been happily married for 18 years. She is the author of Real Women Send Flowers, Why Men Commit and The Second Time Around and has appeared as guest “relationship expert” on The Oprah Winfrey Show as well as othertelevision and radio programs.

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