Questions that tell me everything I need to know about a person

(It’s not your star sign. It’s your sad-day TV rotation.)

This is episode 19 of my mini series: ‘Office Hours’ which shares a listicle look at what’s in my notes app & on my mind. You can expect these on Saturdays, with the exception of the last weekend in the month which is reserved for my monthly unfiltered column. These will be under 5 minutes to read or listen to.

There are certain questions that unlock a person faster than any dating profile, zodiac sign, or Enneagram ever could.

I’m not asking about your five-year plan. I don’t care what college you went to. I’m not even asking what you do for a living, I’m asking who you are when your walls are down, your sweatpants are on, and no one is watching.

These are the questions I’d ask if we were killing time in a Sephora line or splitting fries on a Tuesday. Some are silly. Some are oddly intimate. All of them? Extremely telling.

Let’s begin.

1. What is your favorite show to watch on a bad day?

I don’t want to know what show you think has the best cinematic production (obviously GOT). I want to know what show you have on in the background while you’re working. What’s your go-to rewatch?

Are you a Brooklyn Nine-Nine person? A Parks and Rec person? Are you a Friends loyalist, or are you a New Girl devotee?

Clearly, there is a winner here, and I’m not going to burden you by spelling it out for you.

2. What would you do everyday if you didn’t have to work?

This is the fantasy land that so many of us dream about. “If I didn’t have to get up and do what I have to do for eight hours a day, what would I actually do?”

And while it may not be tangible or practical, like how you go on vacation and think you’re going to dedicate all this time to reading books or developing a new hobby, the reality is you probably just end up doom scrolling, which no-judgement, I truly believe is a form of self-care at this point.

But what do you imagine yourself doing in that version of your life?

3. What quality do you love most about yourself?

As humans, we are so easily critical of ourselves. We notice our shortcomings the most. We make mental lists of everything we wish we could do better.

But the real question is how quickly can you answer: What do you love about yourself?

Is it your wit? Your humor? Your perfectly symmetrical eyebrows? What is it about you that makes you so great?

4. What kind of texter are you?

Do you reply in all lowercase, 0.2 seconds later, with no punctuation and 6 chaotic messages in a row? Or do you disappear for 3 days and come back with a thoughtful essay, pretending nothing happened?

Do you send voice notes like they’re podcasts? Or memes as an emotional check-in? (Just curious. Not judging. Unless you leave me on read.)

5. What do you pretend to like, but actually don’t?

Group trips? Negronis? Reading before bed?

We all have something we feel like we should like, because it’s cool or classy or aligned with some version of ourselves we just aren’t.

I want to know what you secretly hate. This is the realest self-awareness question I know. Mine is going to concerts. Unless I’m in a box with reserved seating, I hate being short and watching the concert through the phone of the person in front of me.

6. How do you act at the airport?

Are you a get-there-3-hours-early type or a sprint-to-the-gate-with-a-bagel-in-hand person? Do you check a bag for a weekend trip or pride yourself on being carry-on chic? Tell me more about whether or not we will ever be travel buddies. Airport energy never lies.

7. What kind of old person do you want to be?

A coastal grandma who power-walks at sunrise? A city-dwelling queen with a weekly martini and a book club that’s actually just gossip? Or the kind who wears caftans and gives unsolicited life advice in line at Trader Joe’s?

This tells me a lot about your future goals. And whether or not we’ll be neighbors at the 65+ pickleball club.

8. What do you buy too many of?

Everyone has a weakness. Maybe it’s fancy candles with names like “Library After Rain.” Maybe it’s water bottles that promise to change your personality. Maybe it’s throw pillows. Maybe it’s anything in the checkout line at Target.

I just want to know the category where your financial discipline crumbles. It says a lot about your aspirational self. And your relationship with delayed gratification. (Or lack thereof, no judgment.)

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Resumes are for LinkedIn. These questions are for people you’d share fries and unhinged voice notes with.

And if you’re someone who orders pancakes for the table and rewatches Miss Congeniality like it’s a personality trait, congratulations. We’re already best friends.

Can you do me a favor? If you like this, will you hit the heart ❤️ at the bottom of your email? I pinky promise it helps me and will only take you a second!

I was having a conversation with my best friend about the favorite kinds of video that we love to binge on TikTok, the one that came out on top was empties. There is something so satisfying about watching someone finish a product to the last drop, especially given the overconsumption and obsession with NEW lately.

This week I finished my second jar of PTR Water Drench Cloud Cream, which feels like an unhinged name for what is essentially the quietest, most polite moisturizer I’ve ever used.

Not all moisturizers are created equal. Some feel like a layer of regret. This one feels like nothing… in the best way. Lightweight, supple, doesn’t pill under makeup, and somehow still makes your skin feel like it drank a whole Stanley.

I originally tried the travel size thinking it would be fine. Harmless. Maybe good for a flight. But I ended up cutting the tube to scrape out every last bit and then immediately bought the full jar. No notes. Will I buy a third jar? Obviously.

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