Dear Dana: Is My Age Ruining My Dating Life?

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 37 years old and still trying to find my person. I’m open to dating people of any age, be it 10 years younger or 10 years older or anything in between. The last two guys I dated, both of whom I met IRL and not online, thought I was in my late 20s, and both ended up dumping me partly because I was older than them. I did disclose my age within the first few dates.

I’ve thus become really insecure about my age and afraid it makes me an undesirable partner, especially for men who want children (which I also want and still hope to be able to have).

With the next person I meet, should I discuss age and children as soon as possible to avoid wasting anyone’s time? Should I set strict parameters around the age of guys I’m open to dating?

I don’t want to give too much importance to age or make it an immediate deal-breaker, but it’s something I’m really struggling with.


Fear of Expiring


Dear Fear of Expiring,

Stop. Just stop. STAHP.

Anytime you find yourself close to asking a question like, “Is this what men want?” or “Is this what men don’t want?” know, in your bones, that you are on the wrong path. You know what all men want? Oxygen. Food. Sleep. Same as all women, same as all gender queer people, same as all infants. The subtext of your question is: “Do all men hate older women?” The more panicked subtext of your question is: “Does anyone want me now that I’m 37?”

Your value does not decrease as your age increases. And, I mean, you’re 37! Do you know how young that is? Ask literally anyone who is a day older than 37 and you’ll discover that it is truly, deeply young. In this case, two men who weren’t ready for you left and blamed your age. And they did you a favor by getting out of your way. Because your age is immovable, and it is well-earned, and it should be celebrated.

But I understand your anxiety. I once attempted to date a man much younger than me. He was a friend of a friend, we met at a party, he told my friend that he thought I was hot as hell, and so I got his contact information and called him for a date. I was 31 and he was 23 but I didn’t care because he was cute and he liked me. I was house-sitting that weekend at a gorgeous home right on the Chicago river that also had a ping pong table in the basement. I brought him with as I stopped by to water the plants, half because I wanted to play ping pong, and half because kissing on a dock overlooking a river is something I’ve always wanted to do.

We played ping pong and he won, mostly because I am terrible at ping pong. Then we sat on the dock and looked at out the moonlit water, listening as the current lapped against the dock. I was waiting for it, that moment where we would lean into each other and kiss. He looked at me and sighed. “I’m sorry,” he said. “I don’t know what I’m doing here. I live with my parents, I drove my dad’s car here, I don’t even have a real job. I just – I’m no good for anyone. You’re older and I just – I gotta go.” And then he got up. And left.

I sat there, stunned. The moon was still reflecting off of the dark water, which was still gently lapping against the dock. I felt like I was going to cry. Was I going to cry? No, I for sure shouldn’t cry over this. But did someone just tell me both that he doesn’t have a car and that I’m too old for him? I went into a tailspin of self-doubt. How was I not appealing enough to at least kiss before you tell me about how you’re not contributing anything to society? I considered changing everything about how I was dating. I considered lying about my age on my online dating profiles. I considered not disclosing my age anymore. I considered only dating men 35 and older. I considered freezing my eggs.

Now, though, I get it. He wasn’t ready to date so he didn’t want to pretend to date me. He thought he was doing me a favor. He was in a tailspin about his own age. He was also having a slight existential crisis.

You don’t need to fix your age, or apologize for your age, or manage anyone’s feelings about your age. Because your age isn’t a problem. You found a commonality between two recent breakups, the age difference, and determined that this is a major negative mark against your dating life. But it’s not.

We are all so mean to ourselves. The idea that you’re beyond your expiration date or somehow not attractive anymore based on your age is preposterous to anyone other than the writers on Married With Children and that tiny, mean voice in your own head. That voice is bullshit, that voice is a lie, and yet that voice is constantly being amplified by women’s magazines and people trying to sell us $100 face cream.

Those dudes who broke up with you? Weren’t your dudes. It’s OK that those relationships ended because neither of those guys was your guy. You’ll know it’s your guy when he hears your age and registers that information the same way that he would register your shoe size, or your zip code. Wow, that is a number and here are you. Let’s go make out.

The man who is your man will love your age. The man who is your man will be overjoyed that you two found each other. He will be ready for kids as well and he will be ready to celebrate the rest of your lives together. But the only way to find your man is to find. Your. Man. And to do that you have to do exactly what you’ve been doing – look. Look hard. Date men who interest you, but know that all of them, with the exception of your man, won’t work out. Don’t worry when they don’t work out because a) that’s what most of them do and, b) that means you’re one step closer to your man.

You’ve earned your age. You’ve earned your experience. You’ve earned the fact that you know exactly what you want. Don’t hide it, or apologize for it. Live it out loud and let those who aren’t ready for it get out of the way.

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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