I just turned 65. Which means I now qualify for senior discounts, mammogram reminders in a slightly larger font, and (if society has its way) an invisibility cloak for women of my age. But I’m not wearing it. Nor buying into society’s ageist nonsense.
The truth is: I’m happier now than I’ve ever been.
After all, I’ve learned a lot from six and a half decades. Sure, I’ve got regrets. But sometimes regret is just a breadcrumb trail to a better, happier life.
With this in mind, I’ve decided to share a curated list of 65 of my regrets. But this list isn’t about shame. It’s about pride in my growth. It’s about holding up each regret boldly to the light and saying: “Thank you for all you taught me!”
Read on and let me know in the comments if you find any of your own regrets hiding in my list.
65 Regrets from my 65 Years of Life… So Far
- I regret pretending to like jazz for that man who didn’t like women.
- I regret shaving my arms in eighth grade because someone said they looked “like a boy’s.”
- I regret saying “yes” when what I really meant was, “I’m afraid if I say no, you’ll stop loving me.”
- I regret ironing. Every time.
- I regret buying “nude” lipstick that looked like I’d just crawled out of the grave.
- I regret spending entire relationships explaining myself. What was I? A user manual?
- I regret not asking for my grandmother’s recipe. And not writing down the story she told while she stirred the sauce.
- I regret not yelling “I’m not done yet” at least once in a boardroom while I worked in advertising.
- I regret laughing at jokes that hurt me, because I wanted to be the kind of woman who “could take it.”
- I regret not keeping the pink cashmere sweater with the hole in the sleeve. It fit my heart perfectly.
- I regret not laughing during sex more often. It was funny at times. It really was.
- I regret thinking I needed to fix people. I can’t even fix the ice maker in my freezer.
- I regret the dinner parties where I smiled too much and chewed too little. Yes, people smiled back. But I often left starving.
- I regret trying to “find myself” in overpriced retreats instead of low-lit diners with friends.
- I regret wasting time trying to understand people who clearly didn’t understand themselves.
- I regret every moment I mistook numbness for peace.
- I regret never buying that antique chair I saw in New Hope, Pennsylvania. It was completely impractical. Like joy.
- I regret deleting the photos where I didn’t look pretty. Those were often the days I laughed the hardest.
- I regret thinking “strong” meant “silent.”
- I regret mistaking self-deprecation for humility.
- I regret trying to “look effortless.” It took so much effort.
- I regret all the times I mistook urgency for love. (Ditto on mistaking endurance for love.)
- I regret not taking better notes when I was happiest.
- I regret the time I gave a second chance to that man who barely deserved the first.
- I regret not keeping a notebook titled: “Things That Didn’t Go as Planned But Ended Up Being Better.”
- I regret deleting my angry emails. They were badly punctuated but emotionally correct. I’d love to reread them now.
- I regret the plants I overwatered and the men I under-loved.
- I regret not whispering to more people: “This is hard, right? Just being alive like this?”
- I regret every time I didn’t order fries because someone was watching.
- I regret how long it took to realize that saying “I’m tired” often meant “I’m sad.”
- I regret not telling her I knew she was lying. I would’ve lost our friendship either way.
- I regret how many apologies I began with “I know this sounds crazy, but…”
- I regret not asking what kind of music my dad liked when he was seventeen.
- I regret thinking I needed a flat stomach to be taken seriously. Like yes, this is my résumé, but how many crunches have I done?
- I regret not speaking up to that one woman at work who said, “You’re so brave for not wearing makeup.”
- I regret not loving people the way they wanted, because I was too busy loving them the way I wanted.
- I regret eating too many salads I didn’t like with too many men I didn’t like.
- I regret not realizing sooner that “being low-maintenance” was code for “Please don’t need anything.”
- I regret thinking I had to be grateful for crumbs. When I could’ve just baked my own damn cake.
- I regret not celebrating more tiny wins.
- I regret confusing people-pleasing with kindness.
- I regret burying my sadness under busy schedules and to-do lists, until it came back louder, angrier, and harder to ignore.
- I regret not asking more questions at the doctor’s office. And not firing the ones who didn’t take me seriously.
- I regret outsourcing my intuition to experts, books, and well-meaning strangers.
- I regret the years I thought thinness was a prerequisite for joy. (Thinness never bought happiness. It just bought pants that didn’t fit the next year.)
- I regret trying to be useful when what I really wanted was to be loved.
- I regret saying “I’m fine” so often I started gaslighting myself.
- I regret all the shoes I bought that doubled as medieval torture devices.
- I regret not buying the inflatable T-Rex costume when it was on sale. That version of me was clearly trying to live.
- I regret not screenshotting more compliments and fewer dumb arguments.
- I regret all the meals I ate quickly, standing up, with the TV on.
- I regret not charging more. For my time. My work. My presence. My emotional labor. (Looking at you, guy I dated in my 30s.)
- I regret giving up on hobbies because I wasn’t instantly amazing at them.
- I regret spending 40+ years trying to be chosen, when I should’ve been just choosing myself.
- I regret waiting until rock bottom to finally admit I needed help. (Turns out, you can ask for directions before you’re lost.)
- I regret giving away the green mixing bowl that still smelled faintly of garlic no matter how many times I washed it.
- I regret not learning how to take a compliment without treating it like a hot potato made of lies.
- I regret spending two decades trying to be “the cool, thin girl” when in fact all I was being was hungry for food and validation while wearing overpriced designer clothes.
- I regret not saying “I don’t want to” more often. It’s a complete sentence. And wildly satisfying.
- I regret every time I Googled a symptom and convinced myself I had six hours to live.
- I regret confusing “he’s busy” with “he doesn’t give a shit.”
- I regret not wearing more hats. Like, literal hats. And possibly metaphorical ones. But mostly fedoras.
- I regret thinking I had to become someone to be loved. I always was someone.
- I regret how long it took to realize that “difficult” women are simply just honest women.
- I regret waiting until 65 to truly like myself. But hey… what a nice surprise.
So, those are my 65 regrets at age 65. And I wouldn’t trade them for anything. Because they led me to who I am today.
Oh… and… for more reflections on regret, joy, aging, living a meaningful life, you can find me at YourToDieForLife.com
Now It’s Your Turn:
What’s one regret (or more) you carry? Drop it in the comments. You never know… naming it might be the first step toward forgiving it.
