Dear Wendy
Dear Wendy

21 Things That Will (Probably) Happen to You in Your 20s

Birthday Cake And Decoration

Last month, I shared a list of things that will (probably) happen to you in your 30s. In a continuing effort to preserve my memory and to add to the record I have of my (distant-ish) youth, I bring you 21 things that will (probably) happen to you in your 20s (the decade of decadence and despair!).

1. If you’re single, you will date someone who will tell you he or she isn’t ready to get serious yet because he or she was recently hurt and isn’t ready to risk another broken heart.

2. In fact, by the time you’re 25, roughly 80% of the people you know will have “been through some stuff” and will “need space” to “get their head together.”

3. Which is basically code for: “I spent a year in a relationship and then I got hurt, so now I want to party my ass off and sleep with whomever I want!”

4. You will regret something you posted on Facebook and feel foolish that anyone saw it before you had the good sense to delete it.

5. If it was a picture of yourself in a swimsuit, you will be in big company.

6. You will, at some point (and probably more than once), Google: “How much should I spend on a wedding gift?”

7. If you are a straight woman, you will, at some point (and probably more than once), Google: “Am I pregnant?”

8. You will, at some point, get into a passionate argument on the internet with a complete stranger.

9. You will, at some point (and probably more than once), Google: “I hate my job.”

10. Because you will, at some point, hate your job.

11. You will probably hate several jobs. (And so will many, if not most, of your friends).

12. So you’ll think about going to grad school (and maybe you even will) or joining the Peace Corps or spending a year working on your preferred candidate’s presidential campaign.

13. I mean, anything is better than working at your stupid job with those stupid people who don’t even come close to understanding your brilliance and aptitude. And your potential!

14. … if only you knew where, exactly, your potential lay.

15. You’ll get your first student loan bill and be like, “Oh, shit.”

16. And then you’ll re-remember your idea about grad school, because you don’t have to pay back your loans while you’re in grad school, right?

17. Plus, you can get more loans! Also: Spring Break!

18. But, God, school is so … tedious! All those papers you have to write! Maybe you could just start your own freelance business doing something you’re good at, like… social media! That’s a career right? Like, social media consultant?

19. So you make a website and some business cards and start a new Twitter Account and and, BOOM!, you’re in business! (This is going to be awesome).

20. And this new focus in your life will totally help heal the broken heart you’re still nursing and will really get your head space in order so, when you’re ready for a relationship again, you’ll be the kind of partner you want to attract!

21. You’ll start going to 30th birthday parties β€” one after another after another β€” where the refrain is always, “We’re getting so old! Can you believe how old we are? OMG, 30! But, I am so ready to say good-bye to my 20s. I heard your 30s are awesome!” And they are. For the most part.

18 comments… add one
  • honeybeenicki July 31, 2014, 4:41 pm

    Some other things that might happen:
    22. You will start getting invited to and attending baby showers/weddings/wedding & baby related parties regularly (and by regularly, I mean ALL THE TIME).
    23. You will start to wonder if maybe you want a baby (or you will end up with full force baby fever).

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  • LadyinPurpleNotRed July 31, 2014, 5:23 pm

    I’m confused on why someone would google am I pregnant. Google can’t tell you that.

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    • Moneypenny July 31, 2014, 5:32 pm

      Google isn’t all knowing?! πŸ˜›

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      • Portia July 31, 2014, 6:15 pm

        Maybe for lists of pregnancy symptoms? I know I once tried to look up what morning sickness might feel like when I was sick. Spoiler alert: there’s a lot of variation. Oh, and I wasn’t pregnant.

      • LadyinPurpleNotRed July 31, 2014, 6:21 pm

        That makes sense…I was thinking literally…for symptoms my mind goes to “what are pregnancy symptoms”

      • Portia July 31, 2014, 6:57 pm

        Ha I’d probably do the same, but now I wish there was one of those pages like isthesilverlineopenyet.com (which I’m sure is one of many pages like it), where it just gives you a yes or a no.

  • Moneypenny July 31, 2014, 5:31 pm

    I have pretty much gone through all of these at one time or another, so you’re spot on. (And I’m almost 2 months from 30.)
    I’ve been at the same job since I graduated at 22, so I haven’t experienced #11 exactly, but I would also like to add, “You tell yourself you should be happy to have this job you don’t really love because everyone says that in this economy you’re lucky to have one, and half of your college friends are working in jobs unrelated to your field.”

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  • Holly July 31, 2014, 5:55 pm

    How about, if you’re single you become very twitchy that you’ll never get married? See 2 and 3 for why.

    (I’m badly trying to convince myself that a long-term/committed partner is in the works, but I’m suspecting I’m a single-for-lifer. Oomph.

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    • Portia July 31, 2014, 6:23 pm

      Yeah, I have a friend who’s convinced herself that at 26/27, she’s gotta start settling. So she’s picked a long distance relationship with a guy she’s not attracted to, because she wants to get married and have all the babies.

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  • Lyra July 31, 2014, 6:40 pm

    You will wonder if and when you will ever be able to afford a house.
    You will learn to hate Sallie Mae.
    You will eat a full box of Mac and Cheese in one sitting with no shame (well, maybe some shame).
    You will go grocery shopping on a Saturday night.
    You will find yourself falling asleep on the couch on a Friday night at 8:00.
    You will realize that some friendships aren’t the same that they once were.
    You will (probably) go through a breakup from hell.
    You will do at least 5 things that scare you (probably more).
    You will realize that some of your coworkers are lazy and you will wonder how they keep their jobs.
    At one point, you will have approximately $4.43 in your checking account, give or take.

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    • Kicia August 1, 2014, 10:48 am

      Eating an entire box of mac and cheese is way easier than it really should be.

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  • bittergaymark July 31, 2014, 6:52 pm

    One of your exes will come out as gay… And it won’t be the one you think.

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    • Something random July 31, 2014, 7:03 pm


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    • Lyra August 1, 2014, 12:28 am

      You mean my flute playing ex who has 98% female friends isn’t going to come out as gay?? Damn, I had been counting on that. πŸ˜‰

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  • Miel July 31, 2014, 7:00 pm

    I’m in grad school and I don’t have spring break πŸ™
    Or national holidays. My school is private and doesn’t think national holidays are a thing. The only one we celebrate is Martin Luther King Junior Day because we are in the south. And then we don’t have the day off on July 4th. Find the logic.

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  • jlyfsh August 1, 2014, 8:24 am

    Facebook came out when I was in my mid-twenties I think? I am pretty glad that most of the early stuff I posted is no longer visible. Definitely some things I did that make me cringe! Sometimes I miss how carefree my twenties were, but man I would definitely not want to go back.

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  • muchachaenlaventana August 1, 2014, 9:23 am

    You will lose two beloved family dogs in the span of a month πŸ™ and be really sad about it because you weren’t able to say goodbye.
    You will wonder if you will ever get a break, and probably despair that you won’t! Yay life.
    Sorry really depressed this morning.
    Def feeling all the friends getting married/engaged/having babies. I am 27 though so it is happening a bit later-the first one of my best friends is getting married next Spring, but I think at least 2-3 more will be engaged by then! Glad it came later for us, and not in the early 20’s.

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  • shakeourtree August 1, 2014, 9:32 am

    I have noticed that as I get into my late 20s, my friends’ engagements are getting shorter. The people that got engaged right out of college or in their early 20s seemed to have long engagements, but now everyone is getting married within a year.

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