15 Reasons Leonardo DiCaprio Should Date A 30-Something Woman

By Anne T. Donahue

I, like you, understand two fundamental truths: first, that we are all going to die. And second, that Leonardo DiCaprio believes he will perish if he dates anyone older than 25.

Well I, for one, disagree. And to plead my case that Leo would only ever die of boredom if he were to date someone like me who is, say, 37, here are 15 points that should win him over and prove that while death comes for us all, it won’t be at the hands of the elderly.

1. A lost capacity to care
I am tired and I don’t care. I mean, I care about my family, friends, and the world at large, but do I care about famous people? Do I think it’s a big deal to date someone who plays pretend as their job? How can I, when I am a person who types on a keyboard for a living, making lists like this one about one of the stars of Titanic? Exactly. I don’t care who you are or what you do, but you will absolutely pitch in for take out when I say so.

2. No working out
I know there are healthy people who aren’t me, and working out is wonderful and releases endorphins, etc. etc. etc., but absolutely not. Today I mowed the lawn in the morning sun and I will be spending the next six days talking about how brave that makes me. This is not the fitness zone, join me.

3. No beach trips
That’s actually just a personal rule because I hate the beach. I’m sorry, but it’s awful. Too much skin! It’s none of my business! Don’t look at me!

4. Wear your cargo shorts, whatever
I used to have a hard and fast rule that cargo shorts were the devil’s uniform but that was before COVID attacked and I could not care less what you wear, provided it’s not those weird hunting-themed coats that make it look like you’re wearing leaves. Leo, your cargo shorts will never be a point of contention. Please pass me plaid PJ pants I plan to pair with my flamingo Crocs.

5. No paparazzi adventures
I don’t know how to call the paparazzi, and I know in my marrow that should they ever find me and think I’m someone they should photograph, my inability to pose for a photo without a prominent double chin will change their minds forever. Stick with me, and no one will even look at you.

6. Normie dates
It’s a Wednesday night, and we’re getting New York Fries at the mall, baby.

7. Hot goss all the time
You don’t know what you’re missing until you hear me talk about my theories regarding Don’t Worry Darling for 24 minutes of every half hour for every day of our fiscal week.

8. The dissolution of the Pussy Posse
I don’t want David Blaine in my home. I will not tolerate Tobey Maguire as a person. This is your chance to shake off the group that’s as upsetting as it is confusing, and begin anew with friends Molly’s Game isn’t based on. You will never have to endure a magic trick or illusion again. The only alliteration you can apply to yourself is Anne’s Angel. (We’ll work on that though because it’s terrible.)

9. Thrift shopping
You ever do this, Leo? You ever join a 37-year-old woman as she sifts through the past and spends a good portion of that time mentioning that she’s got a coupon? For 20%? Because that’s a pretty decent discount, if I’m being honest. You can use it too, if you want. But I call dibs on the soft men’s plaid tops.

ABOVE: Just a few of our fave Leo movies (clockwise): Titanic (1997); Romeo + Juliet (1996); The Wolf of Wall Street (2013); Revolutionary Road (2008)

10. A meaningful relationship with Imodium
That’s right: you hit a certain age (as you know) and it’s over. You can eat what you like, but you will likely revisit it sooner rather than later. Fortunately, I pack. And instead of pretending your tummy’s doing a-okay, with me you can make direct eye contact while silently mouthing out the words, “It’s time.”

11. The nineties
Guess what: I was there. I remember it. We can share memories.

12. Not going to things
You know how many professional events I plan on going to this year? Zero. I want to go to nothing. As Kelly Bundy once said, “I want to do nothing, I want to be nothing.” Which means no more red carpets. No step and repeats. No photographs or speeches or fodder for Page Six. I would rather eat my own hair than attend something people expect me to wear high heels for. My body is sore constantly and I have the attention span of a gnat. Let’s go get Big Gulps and talk shit.

13. Talking shit
At 37, I am excellent at talking shit. Granted, it is about nobody you would ever know, but imagine the delight you can take in learning all about my neighbour, Shirtless Tim, whom you will never meet, but who you will know is constantly shirtless in his front yard for no reason, bless his heart.

14. I am proof that you will not die if you do not date a 25-year-old
If you spend 15 minutes with me as your girlfriend, you will soon realize that you actually seem younger and less weird. Which isn’t to say anything against 25-year-olds: I was one. But imagine the youthfulness that comes with me needing to change into “my comfy clothes” upon arriving home (large sweatpants, a t-shirt big enough to live in). Imagine the Benjamin Button effect of a grown woman holding her cat and writing a song for him on the spot, urging you to join the rousing chorus of “this is my son!” Think hard about the energy you’ll conserve when instead of passionate lovemaking, I say that it’s a Tuesday night for heaven’s sake, please show some decorum. Think of how comfortable you’ll be when you realize that so much of your life can now exist in elastic waistband pants.

15. No yachts
This has nothing to do with age. I do not trust the sea.

Need a little more Anne? Read more from Anne T. Donahue right here!

Tags: Anne T. Donahue, Leonardo DICaprtio, top story, topstory

Related Posts

Previous Post Next Post


  1. Avatar
    • As You Wish
    • November 4, 2022

    This was hilarious! I laughed out loud several times. Loved the wry sense of humor, a really enjoyable read!

Leave a Reply

Your email address will not be published. Required fields are marked *