5 Questions You’ll be Asked if You Date Someone Twice your Age

I dated a 63-year-old and now you all have to suffer.

Eliza Boyd Brown
Hello, Love
3 min readMar 5, 2024

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1. Is that your mom/dad?

Brace yourself because dating someone twice your age basically guarantees that some brave soul is gonna hit you with this question when you least expect it. Yes, even if you and your partner look nothing alike. Yes, even if you’re gazing lovingly into each other’s eyes while holding hands.

Unless you’re straddling each other like two unchaperoned preteens outside of an Urban Outfitters, strangers are going to have a hard time assuming you’re romantically involved.

Pro Tip: Having a funny one-liner prepared for the occasion will save you several minutes of awkward silence. Trust me. The first time someone asked me if my ex was my dad my only response was an involuntary dry heave.

2. How did you meet?

Every couple gets this question at some point. But when your partner is visibly older than you, people don’t ask how you met in a playful, killing-time-between-courses-at-the-dinner-party kind of way. They ask like seasoned detectives who’ve already matched your blood to the DNA that was found under the victim’s fingernails.

And the worst part is, whenever I tried to explain our boring little origin story (we met in a hallway on a Sunday afternoon) I’d get these thinly veiled incredulous stares. Sometimes they’d even throw in a little “Oh!” to let me know they’re super surprised we didn’t meet on SugarBabies.com.

3. What’s the sex like?

I can’t tell you how often this came up. I literally can’t because I had to stop counting for my own safety and the safety of those around me. It’s not the question itself that bothered me. It was the elbow-nudgy, wink-winkiness of the tone that made my soul want to exit my body and take up residency inside the nearest American Girl doll.

Listen, I get it. People who don’t have experience with older partners are naturally going to wonder about the, umm, physical mechanics of the relationship. I don’t have an issue with genuine curiosity. What I do take issue with is the idea that people are allowed to treat May-December relationships like a goddamn Biology 102 course.

4. What do you guys even talk about?

Apparently, any person more than ten years apart from you in age is incapable of holding a conversation with you or having any common interests. It’s simply not possible. Delete your grandma’s phone number, guys. Your relationship is a wrap.

5. Wouldn’t you rather be with someone your age?

First of all, WOW. The GALL. Secondly, this question assumes that:

a. You set out to enter into a relationship with someone older and now you hate it but can’t (or won’t) end things

or

b. You happened to find yourself in a relationship with someone older and now you hate it but can’t (or won’t) end things

Either way, this question is condescending as hell. Outside of a mail-order bride situation or someone blinking S O S in Morse Code, people should simply assume that you actually want to be with your current partner. But they won’t, so practice that polite laugh now, my friends. You’re gonna’ need it.

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Eliza Boyd Brown
Hello, Love

The only bitch brave enough to finish the glass of wine even when it tastes corked.