Running my hands down my jeans as I waited for a drink, I thought, “Can a 22-year-old even be underdressed?” In my corduroy blazer and dark-washed jeans, I was the youngest person in this Boston theater by a generation, the seemingly lone millennial delegate for an evening meet-and-greet with Fran Lebowitz before her onstage conversation. This V.I.P. access came at a higher cost, but I figured if I nixed buying almonds for a few months I could balance my budget.

I’d come alone, not having any friends who were eager to drop $100 to see Fran wax acerbic on secondhand smoke and Rudy Giuliani. But being alone was preferable. If I’d brought a friend, I might have felt forced to talk with someone I already knew instead of eavesdropping on all these people I didn’t.

Settling into a seat with my $17 glass of pinot noir, I overheard a woman say, “How funny you bring up Maria Sharapova. We watched a months-old Charlie Rose with her last night. So self-serious.”

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It all felt impossibly mature, with my fellow attendees seeming so intellectual and arty with their drinks cradled atop world weary wrists. I had never felt older. And I had never felt younger.