Dear twenty-year-old Caroline,

I know you’re feeling insecure about your bangs, but you will look back at the photos and like them. More importantly, I know that you’re wondering what you’ll do if this relationship ends but it will be okay. One day he and his wife will send you and your fiance a LeCruset citrus juicer as a wedding gift and the note will read “may all your citrus juicing be joyful” and you will almost cry—but not because you miss him but because everything worked out for both of you and that’s kind of beautiful.

Dear twenty-one-year-old Caroline, 

I know it’s hard not having the whole family home for the holidays, but it will get better. The way to feel better is not by kissing your closest male friend. He’s gay, and you should already know that. But don’t worry, you’ll both be able to laugh about it later. 

Dear twenty-two-year-old Caroline, 

Congrats on graduating a semester early. Good thing you listened to Mom and took AP Calculus senior year of high school so you never had to take a math class again. Also, that guy from poetry class you’ve been spending a lot of time with is not over his ex-girlfriend. He’s also lying to you. Say goodbye and try not to miss his laugh too much. The only laughs you will really miss later are those of the girls you live with. Cherish them and keep in touch after graduation.

Dear twenty-three-year-old Caroline, 

It’s okay to admit that you’re as lonely as ever and that the timing surprised you. 

Dear twenty-four-year-old Caroline, 

I know you’re feeling skeptical, but moving to Budapest was a great idea and this is where you will learn to be brave. The girl you live with will teach you how to be a good listener and a question-asker. It was brave to spend almost a grand to fly home for the NYC Teaching Fellows interview. It was brave to call the guy you’ve had a crush on for ages from the airport and leave that voicemail. It was brave to sign up for the half-marathon when you’d never run more than three miles at a time. Remember when you left Michigan and you cried your eyes out because some of your closest friends were so cold and judgmental to you that they wouldn’t even tell you goodbye? Turns out it didn’t actually matter that much. Weird, right?

Dear twenty-five-year-old Caroline, 

You’re an idiot but I still love you and luckily so does your boyfriend. Teaching in NYC gets better. You might suck at it now and have no idea what you’re doing but this does not mean you are a failure as a human being and are actively harming the youth of America. And binge-drinking on the weekends won’t make you feel better. Going to church might. 

Dear twenty-six-year-old Caroline,

These things take time. Be patient and forgive yourself.

Dear twenty-seven-year-old Caroline,

Quit your job. You’ve put up with your assistant principal’s bullshit for long enough. You will find a new school, and it will be much better there. Did you notice that you found the courage to quit after you became vulnerable enough to ask people to pray for you? 

Dear twenty-eight-year-old Caroline,

People are going to give you a lot of advice. Remember to listen to yourself, too. When you take time to reflect, breathe, and self-assess, you’ll find you know a lot more than you think you do. 

Dear twenty-nine-year-old Caroline, 

You’re about to be thirty. Stop googling “do jade rollers actually work” and just be grateful. Keep crying on the subway when you hear that one hymn because it reminds you of how much you have to be thankful for. Maybe reconnect and/or prioritize the people who mattered most this past decade. Maybe don’t forget anyone either. Stay humble, and see everything as a gift.


  1. Kyric Koning

    Thanks for this. There’s a lot to listen to here.

  2. Alex Johnson

    I feel like twenty-five-year-old Caroline and I would have a lot to talk about. Also, your title is the best.


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