Encore: May-December Romances

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Cheryl and Steve are no longer dishing out new advice, but we're listening back to episodes we love every week. This episode was originally released October 20th, 2016.

Age is just a number in many contexts, but when it comes to finding long-lasting love, an age gap between partners can greatly impact the course of the relationship — both in positive and challenging ways.

The Sugars discuss those so-called "May-December" romances with the help of Lucinda Franks, a Pulitzer Prize-winning journalist and author of the memoir Timeless: Love, Morgenthau, and Me, which tells the story of her marriage to New York District Attorney Robert Morgenthau, who's 27 years her senior.

Dear Sugar,

I am a 25-year-old single woman nearly done with graduate school. I’m on the search for a single man within my age range, but I often find myself attracted to men in their late 30's to early 40's. I don't intend for this to happen. I met a man at a bookstore recently, and we went on a lovely date. When we realized the age gap was more than 12 years, we mutually decided not to pursue a relationship and remained friends. This pattern has repeated itself with different men. And yet I find, when I try to date men my own age, they’re unavailable. Either they have partners or they can’t keep up with me in terms of emotional maturity. Would it be a waste of my youth to experiment with older men?

I’m an independent woman with financial stability who is still discovering her voice in many ways. I’m scared that dating an older man would interfere with this process of self-discovery because they have already found their voice or, at least, are more settled in a version of who they are. I’m concerned about what effect such a power dynamic will have on me. 

Another fear I have about dating an older man is that if it worked out, I’d have to face the possibility of living the last 20 years of my life alone. I’m not looking for someone to parent or financially support me; I’m looking for a partner. Am I making a mistake by not exploring a May-December relationship?


May-December Curious

Steve Almond: We talk about age, but really, in relationships it’s about power — the power to create your own identity and to be recognized fully for that, rather than hooking your wagon to somebody else’s route. I thought about Louisa May Alcott’s “Little Women” as I was reading this, and it’s such a fascinating story. Jo is the writer in the family, and she has an appropriate partner — the neighbor, Laurie — who’s her age and is in love with her, and Jo decides that she doesn’t love Laurie. She winds up with Professor Bhaer, who’s twice her age, doesn’t have money and is a German immigrant. But what does he have? He knows that Jo is a writer, and he knows that he wants to help her find her voice. So in a certain way, he’s exactly what she needs. Whatever man is on board with that and recognizes that it’s part of his job in the relationship — to help you find your voice – don’t look at the demographic chart. It doesn’t matter if he’s 50 or 25.

Cheryl Strayed: You can’t make decisions about people when you’re thinking about them as categories rather than individuals. I think you should date people you like and people you find interesting and attractive and compelling, no matter what their age is. Also, you say, “If it worked out, I’d have to face the possibility of living the last 20 years of my life alone.”  That presumes that your life is going to go along this course that you get to control. You actually don’t know when you will die. You don’t know when your future partner will die. You don’t know what sort of health you’re going to be in. Anything could happen at any minute. So don’t over-predict your life. Just go out and connect with people who spark your sense of attraction and desire and adventure and all those good things you look for when you’re looking for a partner. Those questions you’re asking should really be asked within the context of a specific relationship.

Lucinda Franks:  I certainly hadn’t planned to end up with a much older man. My dream had always been to find a person my own age, with my own interests. I was in my mid-twenties and a journalist for The New York Times when I interviewed the district attorney of New York, Robert Morgenthau. He was about 53 at the time. I was a hippie, and he was an icon of the establishment. One night, he asked me on a date. I thought he wanted to sell me a story, but he had other ideas. He asked me to a party at Arthur Schlesinger’s house on behalf of Jimmy Carter, who was running for president. I dressed up in my best silk-patterned blouse, my bell-bottoms and my platform shoes. We walked into the Schlesinger home, and there were these women in silk and satin. They looked at me like I was homeless. I turned around and started to walk out the door, and I walked right into Jackie Kennedy Onassis. Everyone looked at Jackie like she was a god — their jaws dropped and they couldn’t stop smiling. I looked up at Bob and he was smiling, too, but not at Jackie. The rest is history. We’ve been together now for 38 years.

Cheryl: Did you have concerns about the age difference?

Lucinda: Absolutely, from the beginning. I was very concerned about his longevity, whether he’d have the energy to be a father, to do the things I did. There was every reason in the book not to marry him.

Cheryl: The two of you have had a long and happy love. But were there things that turned out to be hard because of the age difference?

Lucinda: There weren’t many challenges until he got to be in his 90's. He, predictably, slowed down a bit. We don’t go hiking or camping or do the things we did before, but we’ve learned to replace those with conversation. I never, never thought he would live this long. I always, from Day 1, lived in fear that he was going to die.

If you want to make God laugh, tell him your plans. Nobody knows what is going to happen. Your 22-year-old husband could have a catastrophic accident or illness. Your older husband, like mine is, could live well into his 90's. There is nothing constant but change. There was something new all the time that kept the marriage alive. We found ways to see and appreciate each other as the young, beautiful people we fell in love with. Sometimes you lose sight of that wonderful person you fell in love with as you age.

Dear Sugars,

I’m a 30-year-old woman, and I think I’ve met the love of my life. She is everything I have ever wanted in a partner — kind, playful, loving, genuine and sensitive. Over the past six months, we have fostered a deep and trusting bond. For the first time in my life, I feel completely safe and grounded in who I am. We’ve started dreaming together about the possibility of home ownership, marriage and children. I am proud to be hers, and I am lucky to be falling in love with her.


Here’s the thing: There’s an age gap. Sixteen years, to be exact. She is 46 and well into her middle age with a whole lifetime of experiences under her belt. Our souls seem to match up and, in many ways, this gap is virtually undetectable.

But as I look down the road, questions and doubts emerge. I am in my reproductive prime and eager to have a baby. She wants children, too, but she will be in her mid-60's with a teenager. Our careers and our separate friend groups are in distinctly different life stages. I still feel young and healthy, but she has health issues that slow her down and could become serious down the road.

Many of my friends are still single and dating; they warn me that this older woman will keep me from excitement. Am I going to regret committing to someone who is so much my senior, especially if the age gap becomes more distinct over time? Am I making a mistake by thinking she would be a good co-parent? Am I going to be missing out in some way, by not moving through life’s milestones with one of my “peers”?

Sugars, I’m a realist. I know I’m still in that honeymoon phase of a new relationship where the dreaming comes easy. I’m patient. I know a little more time with her will reveal more answers. But I also feel a great responsibility to not hurt her later if I’m having doubts now. Should I trust my gut here and stay where I am? Or should I think again and look for someone my own age?

With hope,

Minding the Gap

Lucinda: I think her concerns are real, and she may be giving up that excitement from her peers, but everybody who has an unconventional marriage in the works has all sorts of doubts. They have to talk about them with the other person and work through it. For Bob and me, it was timeless. I was delighted in the wisdom he had at his stage of life, and he was delighted by my youth and my energy.

Steve: One of the parts of “Timeless” that’s very moving, Lucinda, is a passage towards the end where you talk about a conversation you had with your husband and he says, “I think you’re angry at me because I got old.”

Lucinda: It is difficult, because you don’t want to lose them. Every slow walk, and every difficulty in picking something up or doing something for themselves, is painful. But it’s not going to make you love the person any less. And when you’re really in love with them, you’ve found the treasure of your destiny, and you do everything to hold onto them.

Cheryl: People are afraid of doing this or that when it comes to love because we want to control our romantic destinies. We want to find that perfect person and live happily ever after. We want the fairy tale. The best version of the fairy tale we can possibly get is the one you have spoken about, Lucinda: finding somebody you love who really loves you back.


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