That happened to me once. When I was 25, I spent ten days in Rome doing things I had never done: staying in hotels that cost more than $50 a night, eating pasta that wasn't Stouffer's. I also met a man who quoted poetry and knew all about wine and astrology and Roman history and which fork to use when presented with several in a fancy restaurant. I thought he was drop-dead gorgeous. He was 80. He wasn't a father figure—he was a grandfather figure. At the end of our weeklong romance, we exchanged addresses and phone numbers. I waited longer than I have ever waited for any man to call me—I was in my 30s before I gave up hope, and only because I figured he was probably dead. But what I learned was, you might think it's not possible to fall in love with someone 55 years older than you, but as with most things you think you can't possibly do—fly an airplane, learn Chinese, move to Paris alone—you actually can.
Still, there's a big difference between being swept off your feet and staying for the long haul. A generation gap makes both people ask hard questions about love, aging, permanence, sacrifice, and family. And when it's the woman who's much older, as I'm seeing more and more often these days, she becomes more conscious of the fragility of her beauty, her fertility, her 20/20 vision.
Dianne Dallin, 46, met her husband Mike, 32, in the middle of the Utah desert, on a canyoneering trip. She was divorced with two children. Her first impression of him was: "He's very cute and very young." She wrote him off. But he was interested in her right away. "I've never been specifically attracted to older women, younger women, whatever," he says. "For me, it's a question of what the person is like inside—which is why the age difference wasn't a red flag."
For a year and a half, they were canyoneering and rock climbing partners, strictly platonic. On Friday nights after work, they'd drive from their homes in Colorado to remote canyons, sometimes eight or ten hours away. She set him up with one of her younger friends, and had a long list of others to introduce him to. "Then, suddenly, I felt myself falling in love, and I really agonized," she says. "What if I tell this guy I want to be more than friends and he says, 'Oh my God, you're like a mother to me'?"
Finally, one night after 12 hours in the canyons and almost a full bottle of wine, she was so exhausted and tipsy that she got up the courage to say, "Do you want to take this relationship further?" He smiled, and they spent that night in their sleeping bags hugging and kissing.
Dianne says that now that she's married to Mike, she worries more about her looks than ever before. "I think that when men date younger women, it makes them feel a lot younger. But for women, being with somebody younger makes us feel older. We're more critical of ourselves. I don't feel older all the time, just when I look in the mirror. When we're hiking, his knees are worse than mine."
Since falling in love with Mike, she has needed to redefine beauty. "When you're with a younger person, you have to think, 'What's going to happen in five years? Ten? Is he going to leave me?' Your answer could be, 'I'm going to get a facelift.' My answer is, 'I'm going to be such a beautiful person inside that it's going to shine through to the outside,'" she says.
Not long ago, Dianne asked Mike if she should get Botox. He said no way. "One thing that makes our relationship strong is the fact that we were friends for so long beforehand," he says. "So when it comes to physical beauty, yeah, you get older, you get wrinkles, you get gray hair, but it's not that big a deal."
For many couples with an age difference, the most soul-searching conversations are about children—whether to have them, when to have them, if there's time. Dianne and Mike talked a lot about family around their desert campfires. "I knew he didn't want kids, and he knew I didn't want any more," she says. "If he had told me he wanted them, I would never have dated him."
For Carolanne McKirnan, 50, and Duncan Burke, 33, who live together in Boulder, Colorado, the question of children is still unanswered. "I'm not interested in having more kids," says Carolanne, who has a 20-year-old son and a teenage daughter. "If Duncan decides children are an absolute necessity, he has to make a decision. We're both aware of that."
Age-gap relationships need to be flexible, and sometimes they're in the spirit of "love the one you're with while you're with him." Carolanne, who wasn't expecting to be in love at all, has learned to take things as they come. When she met Duncan two years ago, she had recently opened a linen store and was more focused on searching for extraspecial percale cotton sheets than on finding romance. "I was a single mother, trying to get my business off the ground," she says. "I write. I try to draw a picture every day. I play the cello." Her attitude toward love and marriage was: Been there, done that.
Then she hired Duncan to design a website for her shop. He's similar to her—an artistic person who likes to play guitar for hours, who prefers quiet evenings and going to bed early over rowdy parties. "He's extremely graceful and very funny and handsome and old-world polite," she says. She could tell he was the kind of guy—and there aren't many at any age—who'd appreciate high-thread-count sheets woven at a monastery in India.
Still, she didn't let herself imagine they could be a couple. Boulder is a town full of beautiful, eligible young women. "The cultural norm prevented me from having any kind of relationship fantasy," she says. "If the older woman has money, she's seen as pathetic because she's buying the attention of a younger man. If she has no money, it seems like she's just hanging on to her lost youth. Those are pretty severe judgments."
But Duncan asked her out to a movie, then wondered aloud, "Was that a date?" Not long after, they spent the night together in her cottage, and he never left.
In the beginning, Carolanne hoped they would blend in with other couples walking down the street. "I was extremely concerned that we'd be treated as an oddity," she says. "Now I don't think about that. The more we're together, the more we look like we belong together."
Liz Banks is 51—but she is a generation younger than her husband, and that's how she likes it. "I did not date men my age," says Liz, who lives in Chicago with baseball legend Ernie Banks, 76. "I am a very driven woman. I enjoyed being with men who were career oriented and comfortable in their own skin. And I loved being challenged by men with more experience."
Liz doesn't need to worry about looking older than Ernie, yet a May-December romance like hers inevitably raises the question of the end. Liz has trained herself not to think about how much time she and her husband have together. "God picks us at all different ages," she says. "When will he take Ernie? I don't know. I don't believe in looking to tomorrow. I really believe in living in the moment."
Many couples say an age-gap relationship can be a great window into other generations—at dinner you might discuss World War II with a much older mate, or blogs with a younger one. "I turned 50 in December," says Elizabeth Yoakum, a graphic designer in Sheffield, Massachusetts, who met her boyfriend, Josh Buell, eight years ago. "He turned 37 the day after my birthday. We have about the same age difference as Tim Robbins and Susan Sarandon." Their circle of friends includes his and hers, young and middle-aged, a wonderful, eclectic, challenging gang. "Josh's friends are all 30-something, and now some of them are married to even younger people," she says. She has never felt self-conscious around them. "It's not as if people come up to me and say, 'I don't like hanging out with you because you're too old.' You don't have to be in a certain age group to know what's hip anymore. We all have the Internet."
But it does help to be of a particular mind-set. "If you're very conscious of how far your relationship is from the norm, then every day you're going to see those differences," Elizabeth says. "I wasn't raised to be by-the-book."
If Chris Crowley, 72, goes by any book, it's the one he wrote: Younger Next Year. He is on a mission to stay as youthful as he can for his wife, Hilary Cooper, 48. Chris rows several times a week, rides his bicycle through the Rocky Mountains and the Dolomites, and spends a month skiing in Aspen every winter. "Older men married to younger women have a duty to stay in great shape and work out like lunatics so their wives won't ever have to wipe the goo off their faces," he says. "Seventy-five percent of aging is rot—you get a little fatter, a little more apathetic, a little more pain racked. But you don't have to go there."
Both say Hilary, a portrait painter, is the wise old parent in the marriage, more fiscally responsible and always the designated driver. Chris is the kid who doesn't worry about debt and dances like a maniac at parties. "From the moment I met him, I knew he was such a young spirit," Hilary says. "He introduced me to the athletic lifestyle. I'd never skied before; I'd never mountain biked; I'd never gone windsurfing. I wore only black. Chris is 24 years older, but he's really so much younger. I am never bored with him, never ever." But, Hilary says half seriously, half sarcastically, "I get sad because he is going to leave me for another woman: death."
"We have different horizons," Chris says. "I know I'm going to be dead way too soon, and it makes me sick. We are inseparable, and inevitably, she'll get left. But hey, that's the deal."
Age-gap relationships warp both partners' inner timelines and long-held presumptions about where their lives are going. Sometimes things are done out of order, just because there's chronological confusion to begin with. Jill Adler's boyfriend, Ryan Freitas, is 27; she is 39. They met at a bar in Park City, Utah, four years ago, and for the first year they dated, she lied to him about her age. "Then one day I had my driver's license out and wouldn't let him see it. He asked, 'What are you hiding from me?' Finally, I said, 'Just look at it. If you're going to walk away, walk now.'"
He stayed. In 2005 Jill really wanted to get pregnant, but Ryan wanted to turn 30 before becoming a father. She told him she couldn't wait that long, biologically. So he made the leap. They weren't married, he was scared to death, yet he still said to her, "I'm your man."
"Think back to when you were 26," she says. "At that age, I didn't want to have a kid, so I kind of understood. But he didn't want me to miss out on the opportunity. It was basically a gift from him. He was doing me this great favor. And I never said, 'Now you have to move in; now you have to marry me.' It was just, 'You are going out of your way to do something incredible for me, so whatever you need to do is totally your prerogative.'"
For all its challenges, an age gap can also provide a chance to slow down and take a deep breath. Sarah Belle, 49, lives in Iowa City with her husband, Haywood, 67. She loves his easygoing pace and low-key, old-fashioned sense of romance. He buys her gifts, but they are more thoughtful than flashy, like a single flower or a new umbrella. "When we were dating, every time I came to visit he'd have licorice—I love licorice," she says. He never tried to wow her with expensive jewelry or clothes—even though, as a successful real estate developer, he could afford to. "He didn't have to prove anything," she says. "When people are younger, they often try to sell themselves." And the prospect of nursing him if he becomes seriously ill is fine with her. "Of course I'll be there to take care of him!" Sarah says enthusiastically, as if she were talking about a cocktail party she will definitely be attending.
I've often heard that love should be easy, that even the hardships shouldn't feel so hard. I believe there's some truth to the Cinderella fairy tale—your partner should be like a shoe that fits perfectly, not one you have to force because you want to live in a castle and wear a tiara. More than anything, Dianne Dallin says, being married to a man 14 years younger has taught her to keep her eye on the essentials: Does it feel right? Is he kind? Do I love him? If the answers are yes, she says, then nothing else really matters.