Dear Dana: I’m In Love With A Much Younger Man. Can We Make It Work?

Dear Dana is a bi-weekly advice column for humans who engage in romantic relationships. Please send your dilemmas, issues, conundrums, assumptions, conflicts, anxieties, worriments, obstacles, complications, predicaments, queries, questions, and any other synonyms for “problems” to

Dear Dana:

I’m a 45-year-old woman, never married, and happily child-free. I live in Los Angeles, where I work long hours in the television industry. It is a career I love, but one that has certainly limited my social life. Until recently, that is. Earlier this year, we hired several new crew members, and one of them immediately caught my eye. He’s smart, funny, gorgeous, and wise beyond his years, which is important because, well, he’s only 30 years old. What started out as innocent workplace flirting turned into coffee dates, which turned into dinner dates, which turned into incredible sex and sleepovers. I’ve been in several fulfilling relationships in my life, but I’ve never felt sexier or more alive than I do right now.

I’m, without a doubt, falling in love with him, but am concerned about our 15-year age difference. Can I be public about our relationship without people thinking I’m a “cougar”? Will he eventually grow tired of me and want someone his own age who can give him children? Or will I get tired of him and miss the company of a more seasoned man? 

I don’t want to end it and break his heart or mine, but is heartbreak where this is leading anyway? What should I do? 


Cradle Robber


Dear Cradle Robber:

There was a concept in the ’70s and ’80s that, finally, women could “have it all.” “It all” referred to having both a career and a happy home life. The term pushed back against the idea that in order to be in the workforce women had to forego domestic bliss. But you still believe that you can only have one or other. How could a woman such as yourself be lucky enough to have both love and a career? Impossible. The gods will surely strike you down for your hubris.

Many, many people have both good careers and good home lives. You don’t have to pick. Your career is fantastic and this man appears to be your man, but in order to accept him you first have to accept yourself.

There is nothing wrong with being 45 years old. There is nothing wrong with being 45 years old and falling in love and having tons of terrific sex. There is nothing wrong with doing those things with a younger man. Will other people call you a cougar? Lean in and listen close: Who the fuck cares? You’ll never know if anyone calls you a cougar or not because horrible people who talk badly about people who don’t adhere to our very narrow cultural definition of “appropriate” behavior are super good about talking where you can’t hear them.

You should never live your life because you’re afraid of what others will say. You want to be yourself, not an amalgamation of lifestyle choices directed by the insecurities others.

But what others will say isn’t the real problem—it’s what you’re saying about yourself. You aren’t a cougar. You aren’t a cougar because cougars aren’t real. The large American wild cat cougar is real, but the older woman sexually preying on younger men is not. You get to date whoever you want without gaining a terrible, sexist name. Cougar is a term used to denigrate women who dare to invert typical male/female age dynamics. What do we call men who pursue younger women? What do we call men who like older women? We call them “men.” Sexual age dynamics don’t change their name and neither do yours.

You choose to pursue your career, one with long hours and constant work. You made the choice that you would live as a single person and find fulfillment in your work. You embraced your choice. And something happens when you’re alone for a long time—you become forceful, able to get things done with nothing but your power. You become able to overcome obstacles without help, because you have to. You become incredibly adept at navigating the world completely on your own, without consulting or needing the input of anyone else. This is a necessary skill, but when you introduce another person into your life that skill suddenly becomes a barrier to intimacy. You are able to thrive in the world on your own, and you are afraid of this new relationship and this new man because you can’t thrive in the same way with him. To have him with you, as your love, you have to change. You have to thrive in a new way.

Accepting love is terrifying. I could never relate to most romantic comedies because they portrayed starting a new relationship as the most amazing time in a woman’s life, while I always found it to be a time full of intense anxiety, worry, and me fighting my instinct to run as far as I could away from my new boyfriend.

The day after my third date with my now-husband, I was in a Chicago laundry mat washing my clothes. It was a Sunday ritual—go to the laundry mat, tuck in with a cup of coffee, and get some homework done. But I couldn’t concentrate on anything I was supposed to be reading. The night before, on our third date, my now-husband had told me that he wanted to be my boyfriend. He was all in. I responded that I was still seeing other people, even though I didn’t mention that they were just first online dates I had scheduled later that week.

I had been dating for a few years with the goal of finding a partner, but now I had a man saying he wanted to be my partner and all I could do was sit in the corner of this laundry mat and weep. I was terrified of saying yes to him because it would mean that we would date and fall in love and live together and get married and have babies. There, in that orange plastic chair, I knew that if I said yes to this man, my life was going to fundamentally change and never be the same again. I was going to stop being me, by myself, independent. I was going to give another human access to me and the ability to hurt me in a way I couldn’t fathom. Alone and safe, or together and at risk: that was how I saw my dilemma.

I chose my husband. I chose what was, at the time, a perceived risk. And in making that choice I had to change. I had to become a part of a couple, I had to gather his input before making decisions that affected both of us, and I had to accept the inevitability that he will break my heart.

Here’s the absolute truth, which you already know: All love leads to heartbreak. Even when you don’t break up, being in love means he will disappoint you and you will disappoint him. You will have to capitulate and compromise. You will have to give in and set your ego aside. Everyone must sacrifice and bend to be with the ones they love.

Which do you want: to be perfectly alone, or to be perfectly at risk? You want to love this man, but you’re afraid. It’s OK to be afraid. The fear doesn’t mean that you’re doing something wrong. The fear means that you’re about to change. Let yourself love this man. Let yourself know the rush and change that comes from the risk of love.

Dana Norris once went on 71 internet dates, many of which you may read about here. She is the founder of Story Club and editor-in-chief of Story Club Magazine. She has been featured in McSweeney’s, Role Reboot, The Rumpus, and Tampa Review and she teaches at StoryStudio Chicago. You may find her on Twitter at @dananorris.

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