The Upsides of Stealing Wine
Ever wondered how to love the embarrassing parts of yourself? First, own up to them.

If you’re here, instead of watching Youtube or Netflix, you probably consider yourself to be intelligent. You might think you’re the type of person that wants to give something to the world. Someone that actually has something to give back to the world.
If you’re so interested in self-improvement, what does reading about dishonesty say about your moral code? You’ve been a bad little reader, haven’t you? Time for your punishment, naughty girl.
You’ve been a bad little reader, haven’t you? Time for your punishment, naughty girl.
No, no, thank you, this isn’t that kind of article. No kink-shaming here, Just moderately long-winded life lessons.
Maybe there IS something good about stealing. Not stealing itself, but the value of sitting with the worst parts of yourself and learning to love them. Or at least, learning to love what comes from them. The change that accompanies self-awareness after you’ve realized what you’ve done, who you are, and how different you want to be.

I’m going to tell you about my middle-of-the-night, crack-head adventure in Walmart and why it turned out to be a very good, bad idea.
Have you ever felt sad? Emotionally drained? Tired? Of course, you have. You’re human.
It’s a Wednesday night and you feel yourself checking out, settling into a grayness. You’re moving through mud as you feel yourself sinking lower into it. And somehow, your discomfort grows, because gradually, you don’t even mind that you’re made up entirely of dull things without any color. And maybe you were always supposed to be sinking. Maybe you were always supposed to be avoiding the color. What do you when you feel like this? Who are you at your lowest point?
What do you when you feel like this? Who are you at your lowest point?
I’m still trying to answer that question. Right now, I like to turn to outlets like meditation, music, and journaling. But that night? That night, I did something very different.
I did what any normal, emotionally stable young adult would do. I decided to become a cartoon.
More specifically, I decided to replicate what I saw in my favorite show, BoJack Horseman. A cynical, animated tale about anthropomorphic animals who repeatedly make questionable choices, and mask the resulting guilt with… more terrible choices.

So at 2 am, I called a Lyft and stepped into the 24-hour Walmart. I picked up a bottle of Rosé and read five chapters of Little Women.
I want to make something quite clear. I have never shoplifted before. Well, except for a pair of Halloween costume sunglasses I lifted from a dollar store because I had forgotten my wallet. I’ve never been drunk before. I have never hidden Rosé in Aisle 15 while reading Louisa May Alcott.
At 3:30 am, I called my best friend and we talked while I was wasted. She laughed a lot. I rambled a lot. I had officially become a Karen. I realized that meaningful relationships helped me a lot more than the alcohol did. Somehow, I walked out of the store without anyone realizing what I had done. I was not a criminal mastermind. I was a lightweight, hungover from Walmart Rosé. I woke up that morning blinded by the light. Not just a Bruce Springsteen shout-out — it hurt to see.
The next morning, my best friend came over with her Not-Boyfriend, a plate of brownies, and a hug. I had admitted my crimes to far too many people, including my Mom-Friend and this very kind brownie-bearer.
Look, relationships in your 20s can be quite complicated, so don’t judge. A Not-Boyfriend can mean a variety of things, including,
- A one-sided crush
- He’s just my friend, but we also make out, and I’m still in love with my ex
- It’s easier to just say boyfriend
I have been privy to most… well, all of these categories. And I would bet a cow-and-a-half that either you or someone you know has, too. Don’t tell me about how cows aren’t something you barter with anymore, as it’s the “21st Century” and we have updated our currency, etc, etc, because I simply don’t want to hear it.
Unfortunately, after finishing the last bite of brownie, I made the mistake of pulling up Twitter. Curse those addictive algorithms. I follow far too many people who tell me how to be my “best self”, which was the last thing I wanted to hear.

On this particular conscience-probing app, I read something from a wise Rabbi named Danya Ruttenburg, who I think of as my Jewish fairy godmother. Mostly because I am only a quarter Jewish and wish I had more of the cultural identity, enough to win an all-expenses-paid trip to Israel. But I am Jew-ish. Not Jewish.
To clarify, Rabbi Ruttenburg is not a magical fairy, but she is a miracle-worker. She wrote that in Judaism, you can complete Tshuvah and Repentance work and get right with God, even if your victim never forgives you. They’re separate processes. Tshuvah means return, like coming back to where you were supposed to be. Part of Tshuvah is accepting the consequences of your actions. That may include willingly receiving consequences from the criminal justice system.
That’s when it hit me, right then and there, like Jiminy Cricket screaming into Pinocchio’s wooden ear. I wasn’t where I should have been. But I could be where I was supposed to be.
Present Me needed to take care of Past Me’s stupidity so that Future Me could be happy. My Brownie Friend cautioned that she didn’t think Future Me would be very happy if Future Me was in jail.
But my Mom-Friend told me, “You can’t overcome something you never let yourself confront or feel.” And that meant that a wise, sage, Dumbledore-type and a Rabbi agreed I needed to own up to my felony. Or misdemeanor. It varied, depending on which Google search I frantically performed.
I checked and re-checked all the possible outcomes for my crimes. Shoplifting. Underage drinking. Loitering. F*cking up your sleep schedule. I was sure that I didn’t want a criminal record. But I had also grown up on a steady influence of Harry Potter and other teen dystopias. Inspired by my childhood love of Gryffindor House, I knew I couldn’t act like a coward.
So I did the only thing I could do. I confessed.

I took an Uber to Walmart, and I walked up to security, and I think I had a panic attack. Every part of me started shaking. Even my spleen. I didn’t know my spleen could shake.
I told the head of security that I stole alcohol at three in the morning, and apparently turning yourself in is not a very common occurrence because security kept saying things like, “Who made you come in here?” and, “You can keep your 12 dollars,” because I had set 12 dollars on a table, which was the price of the Rosé. And security shuffled awkwardly, and I shuffled awkwardly, and I would have rather melted into the floor than spend another minute in uncomfortable silence. Eventually, they told me they would check the security cameras from the store.
While the Asset Protection Officer went to review the footage, I got a text from my Mom-Friend.
“Hope everything turns out ok! I also kind of hope there’s enough of a consequence that you don’t steal again! But either way, I’m really proud of you.”
So there I am, waiting for a painstakingly long time, with my criminal record hanging in the balance, my future hanging in the balance, and my mom-friend is hoping I’ll get prosecuted. Was her opinion justified? Yes! Did it make me feel more like Chidi Anagonye, beloved character from renowned moral philosophy sitcom? Possibly!
The security officers returned.
I thought I was breathing underwater, everything felt so surreal. But they smiled at me. They looked at me, as I was crying, and told me to be happy. To relax. And they gave me excellent advice.
“Don’t go doin’ dumb sh*t.” Which was fair, since I had definitely been doing just that.
They wrote my name down, and copied my driver’s license number, and told me they wouldn’t be pressing charges or banning me from the store. Because they valued honesty. Or maybe, because I am white. I don’t know for sure.
Is there an upside to stealing wine? Is there a benefit to realizing who you are at your lowest point, and who you want to become? If you consider yourself an optimist, like I do, you will find the bright side. If you’ve ever wondered how to love the embarrassing parts of yourself, first, own up to them. And even if you don’t love your flaws, you might at least love what you’ve learned from them.