What She Wants

Etiquette For Dating Someone Way Older (Or Younger) Than You

As someone who's done both, the Truly Rich Lady shares what it's like when there is an obvious age gap between people who are dating.

Dear Truly Rich Lady:  

I've found myself in a relationship with a man younger than I am.

Let’s say I am in my late 30s (okay—I am 40) and he is in his early 30s (he’s 27!), and we are so much in love. I think.

I am not bothered by the age difference, because I put more weight on chemistry and compatibility, and within these parameters, we are a perfect match. We watch the same types of Netflix series. We have the same political opinions (for the most part). We are both morning persons. We hate cats equally. We love the outdoors.

But sometimes, I cannot help but feel I am doing something wrong. There are stares, of course. I look younger than my age thanks to my meticulous self-care, but I can’t say I can pass for a 20 year old. And I also think about the future. Will I be around to see our children grow up? Will he tire of me when I become a really old bag?

We just celebrated our first year anniversary. I am happy, but there is a voice that lingers on in my brain.

Truly Rich Lady, I ask if my December-May romance is worth it?


Not An Old Bag Yet 


Dear Young Bag:

Now, I am not one to kiss and tell, because I am a proper lady—a Truly Rich and Proper Lady, in fact—but I will go ahead and say that I have been on both sides of this coin. I have been the young beauty on the arm of an older man, and I have been the more advanced (not old!) woman with a hot new piece.


I share my notes with you. 

You as the Younger Woman

There is much excitement in a relationship with an older man. I feel so—what’s the word?—pretty. This may seem a simplistic analysis of an extraordinary relationship, but that’s how I felt.

How beautiful I must be for this gorgeous older man, who knows poetry and art and manners, to choose me, a person who is young. How special I must be to be chosen as his (maybe secret) girlfriend.

I loved how he knew so much about the world and about life. The fact that he paid for everything and showered me with gifts, like a just-because-it’s-Tuesday Birkin and a summer trip across Europe, made my heart flutter, too. It felt so good—so good to be true.

The wheels started to fall off when his big ol’ brain became a drag. He was keen on very serious things such as babies and what kind of house we should get (Mediterranean! Yuck!)—things that I, as young person, did not want to entertain at that moment.

I was a proper young lady but my youth also meant that I was unripe. And by this, I mean bratty. We parted ways in the most dramatic way: shouting in the rain. Maybe I threw a delicate Alhambra bracelet, another just-because gift, somewhere in the bushes.

Later on, when I was—as the legendary Miss Jackson put it—ready to love him that way he loved me then, it was too late. He was married (or maybe he was dead?). I look back with sadness at our time together, because I am forever sore that I never found that Van Cleef bracelet in the bushes.

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You as the Older Woman

I'm going to lead with the obvious and say that my younger man was easy on the eyes, and I loved that. But more important than that dazzling face, he was easy company. He was not a moody curmudgeon or a run-of-the-mill old fart like most of the men in my circle. He was always full of joy. In fact, when we met at one of those pretentious cocktail parties, his opening line was a joke. The joke was lame, but I found him interesting.

He just made me feel young again. I did things that I’ve never done in my life like, say, laugh—the kind of laugh that starts deep inside the belly and ends with a snort. I traveled with him to out-of-the-way places like a secret beach that only had huts for accommodations. So at ease I was in this relationship that I started to wear flats, the rubber ones.

Does my experience mirror yours? Now, I bring your attention to what may happen:

Because I was the older and, I think, wiser party in the relationship, I was more intent on the long haul.

Fertility and mortality were the things that came to the fore, at least on my end. Did he want babies and could I still have babies? Did I need to get an extra special session of PicoSure? Would his eye ever wander if my hair started to thin? And did I have to exercise forever just to keep up?


I was worried about the future and, as I found out, he wasn't even thinking about anything beyond next Tuesday. When it was clear that our goals would not intersect, we ended things. 

I, Who Has Survived Both

A quick note: I also find a parallel between relationships of differing ages and relationships of different wealth. In both, there is an element of power at play. One has more, the other has less, and the one with less power usually ends up appearing more desperate.

Did I try very hard to please my older man so that he would not leave me? And did I assert my dominance, making all the decisions in my relationship with a younger man? Yes and yes. It's the awful truth.

Two more truths: If you're looking for something wrong, a speck in the dust, a crack, an errant thread, you will find one. But if you look at him and believe, without question, that you belong together, the numbers will not matter.

The wost thing is a tentative heart, a love that is unsure. If you have doubts and cannot work through it, seek happiness elsewhere. 

With Love,


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C.C. Coo
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