Very Serious: How Do You Know Where to Live?

- Very Serious: An Advice Column By Kelly Conaboy -
Very Serious: How Do You Know Where to Live?

Kelly Conaboy is writing an advice column for Dipp readers. It's going to be very serious. So serious, in fact, we named it Very Serious: An Advice Column by Kelly Conaboy. Just email her at with your most crucial conundrums and each week, Kelly will solve one lucky reader's biggest problem.

Previously, Kelly has tackled the stars, how to buy a couch, how to get over a break up, how to ghost, how to update your computer, how to ditch your friends' babies, how to move, what to cook for dinner, and how to quit Twitter. Today, she tackles the existential crisis of moving.

Dear Kelly,

I moved away from NYC during the pandemic (not to the Hamptons…) and now I’m not sure if I should come back. Everyone, including me, has acted like it’s inevitable, and THE logical place to live, but… is it? How does one know where to live, in the absence of job requirement/parenting/or other obligation reasons?


Hi Katie,

Oh god, I don’t know. Let me think.

First I’d like to say that your situation is enviable. It seems like you can live anywhere. That’s exciting!

Okay, did that exclamation point make you feel happiness? I hope it gave you a moment to feel a spark of joy, because I understand — too many options can be debilitating. I once knew someone who became a vegetarian in part because they wanted fewer choices at restaurants. I relate to this mentality. In my neighborhood of Brooklyn there is essentially one coffee shop that isn’t very good; this to me is much more desirable than if there were several coffee shops of varying quality. If you want coffee, you go to the coffee shop. No decision making involved. Peace. Tranquility. Mediocre coffee.

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