34 Regrets I Have About The Past 34 Years


The Google Dictionary defines regret as “a feeling of sadness, repentance, or disappointment over something that has happened or been done, especially a loss or missed opportunity.”

For many years, when the topic of regret came up, I would confidently say, “if I had any regrets, that would mean that I wish this very moment was different, because every second in my life has led me to where I am right now, and I’m great right now, so nope, no regrets!”

I was kind of smug in my twenties.

Do I have regrets today? Absolutely. And yes, that means if I could alter some things in my past to make this moment different, I would be on board with that.

I don’t dwell on these things. I don’t beat myself up over them. My life is fine. I haven’t reached a low point of no return. I forgive myself, everyone else, and keep moving forward. I brush the dirt off my shoulders faster than you can say Obama wishes he was Jay-Z.

But if, in some magical twist of fate, I was visited by Takeback, the Regret-Erasing Elf, here are the first thirty-four things I thought of that I’d like to fix.

  1. I regret buying that $500 Hermes bangle. It didn’t make me feel any better at the time, and now it makes me feel dumb when I wear it. It’s a badge of peer-pressure consumerism.
  2. I regret unfriending some people on Facebook in a bout of short-sightedness, not realizing that I would very much like to stalk them later on, and I’d have only myself to blame for being prevented from such activity.
  3. I regret those times I felt smoking hot and flirty, went home, looked in a mirror, and discovered that I was a hot mess from head to toe; with eyeliner goop in the corner of my eye, my zipper unzipped, or something in my teeth.
  4. I regret being too young to truly appreciate my grandparents before they were gone.
  5. I regret using my work email address as my personal email address for years just because having two seemed like a hassle, and I wasn’t wise enough to foresee what a truly disastrous end that would have.
  6. I regret the four times I invited myself over to that weird apartment on the Lower East Side, because nothing good ever happens there, yet I can’t seem to retain that information.
  7. I regret adopting that puppy. And then giving it back. I don’t wish I had kept it. I just wish I had never taken it home in the first place.
  8. I regret any time I have ever treated someone else’s feelings casually and caused them pain. I regret every time I acted with a lack of patience and humility.
  9. I regret not memorizing every sincere hug, kiss, and snuggle in my life. I regret not storing them up in a bank of affection for the days I need to make a withdrawal.
  10. I regret the three years that I thought French manicures looked upscale.
  11. I regret not approaching that beautiful boy in the bar and introducing myself. I knew when I posted that missed connection that he would never, ever see it.
  12. I regret being immature in a lot of situations that should have been handled with a little grace and class, neither of which I possessed at the time.
  13. I regret asking for the credit I deserved in my professional life several years too late. I regret not ensuring that I got what I had earned every single time, like a man would have, without apology.
  14. I regret buying those big bags of candy at the drug store, telling myself I’ll share with the whole office, and polishing them off by myself.
  15. I regret moving away from New York in 1999 after having a rough couple of weeks.
  16. I regret going to school for theatre and photography instead of getting a degree that taught me tangible, real-world skills.
  17. I regret every minute I have wasted wishing my brother and I were friends.
  18. I regret wearing Birkenstocks for my entire tenth grade year, and I regret all of the days I still wear Uggs. I am simply powerless over comfortable footwear.
  19. I regret losing one of my very best friends over pride, ego, and money.
  20. I regret throwing a brat-style tantrum and screaming at my parents, “I wanted to do it my way, all by myself” when they surprised me by generously decorating my first apartment.
  21. I regret communicating to my friend’s boyfriend that he had hurt my feelings by flipping him a middle finger in the street, because it cemented me out of his life forever.
  22. I regret all of the hours I have spent in the sun, trying to tan like the cool kids, because my people are not meant for the sun and I will, as a result, be having suspicious moles removed for the rest of my life.
  23. I regret the $30,000 that I ran up in credit card debt in one year, because it took me seven years to pay it off. I regret upsizing to a bigger apartment and filling it with more stuff every time I could afford to.
  24. I regret repeatedly losing my grip on the big-picture perspective and allowing myself to feel as though my life and my problems are more important than they are.
  25. I regret buying and reading women’s magazines for much of my young life, and believing them when they told me that I wasn’t as skinny, pretty, stylish, or sexy as I should be.
  26. I regret that year I listened exclusively to Garth Brooks, Lyle Lovett, Metallica, and G Love & Special Sauce.
  27. I regret vowing to spend the rest of my life with someone as if I could possibly know what lay ahead in the future.
  28. I regret being obnoxious at summer camp.
  29. I regret telling that boy what I thought of him on our first date instead of being patient and playing it out a bit longer.
  30. I regret not being able to let go of some small things, and letting go of some big things much too easily.
  31. I regret embracing complacency and forgiving my laziness by deeming it “being patient with myself.”
  32. I regret every time someone talked me into watching Intervention, Hoarders, Oz, Lockup: Raw, and Cops, because those shows depress me for days.
  33. I regret those times I acted like I knew of the author/artist/director/philosopher people were talking about because I was too insecure to own my ignorance.
  34. And of course, I regret that day I neglected to wear panties and my skirt fell off at the Coffee Bean.

I’ve learned from my stupid mistakes.

The challenge is to not repeat them.

It’s not easy to avoid homeless pets, remember my underwear, and resist the constant urge to be a bitch all at once.

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image – ~*Dawn*~