Tailwinds and Tall Tales

New York, Take Two (Because the First One Was Cursed)

Quick trip to New York with one of my besties, Alex. This was a do-over. Back in November, Alex landed tickets to The Late Show with Stephen Colbert for election night. We were pumped—Colbert, plus & Juliet (featuring a kid from Charlotte as Romeo), The Drew Barrymore Show, and even Kelly Clarkson. A trifecta of shows, squeals, and probably tears.

So, we booked the non-refundable hotel (because… cheaper) and flights, only to have Colbert cancel on us. We’re pretty sure they knew how the night was going to go down and didn’t want a live audience crying on camera. But we’d already voted, and what else did we have to do? We decided to go to the Big Apple anyway.

Now, here’s a crash course on the “free” TV show ticket process: shows use 1iota to manage tickets. You apply, they assign you a date, but even with a ticket in hand, you’re not guaranteed a seat. You need to show up hours early, clear security, hit the bathroom, and surrender your phone to the void.

Day one back in November: Drew was our first show. We scoped out the venue early, as two Girl Scout Leaders would, and met a bald, ex-cop type security officer who told us to arrive 30–45 minutes early. So obviously, we came an hour early. We got in line—General Admission but it was much longer than the security officer explained. VIPs and Priority people were already there, looking smug.

A headset-wearing intern scanned us in, took our IDs, and delivered the news: “You might not get in, but if you don’t, you’ll get Priority next time.” Which is like being told you didn’t win the lottery, but hey, next time we’ll give you a faster losing ticket. Sure enough—we got cut.

We adjusted our expectations and headed to The Daily Show. Showed up early, made friends in line (Canada, Upstate New York—we were basically at the UN), and… got cut again. But we were Priority now, baby. 

Feeling rejected we went back for dinner and to our hotel. The good news was the next night we got to see the Charlotte kid in & Juliet, had good food, and got to hang with Annie and a friend’s daughter. So, not a total wash.

Fast forward to this spring: Priority tickets in hand for a Monday taping of The Daily Show. Jon Stewart night. Big deal. We grabbed morning flights, planning to drop bags, eat lunch, maybe do a little city stuff before heading to the studio. Smooth sailing… until check-in.

Mechanical delay. Next flight: sold out. Chad couldn’t swoop in with the plane because of some airspace drama (I don’t know either). So, we decided to wait it out. Things looked up—they boarded us. Then right as we were stepping onto the jetway, a woman in front of us said, “I just got a text—this flight’s delayed another hour and a half.”

Do I want to sit on a motionless plane for 90 minutes? I do not.

We hesitated. Jetway person insisted—“We’re going!” So we got on. Then, just as we were about to leave… everyone off. Round two of baggage wrestling began.

Back to the lounge. Just as we watched the change out from breakfast to lunch and contemplating what I was going to eat next, our phones dinged—“Flight boarding again!” At this point, we’d mentally accepted we might not make it, but we were going to keep trying.

Then something miraculous happened. That plane must’ve grown wings on top of its wings. Flight time was supposed to be close to two hours. We got there in 1 hour and 25 minutes. Bless the wind gods and caffeine-fueled air traffic control.

We beelined to the hotel, tossed our bags down, and stopped at a café for what might’ve been the best almond croissant of my life. Sustained by flaky pastry and adrenaline, we got in line at The Daily Show studio by 3:30. There were already 28 people ahead of us.

Checked in. Got our numbered tickets (#29 and #30). Bathrooms, security, holding room. We watched an old episode while waiting. At 5:00 they brought us into the studio. Inside, no phones. The interns assigned our seating. Ours? Pretty perfect.

The warm-up comic came out at 6:00 to hype the crowd. Jon Stewart arrived, took a few questions, and the taping began. It felt exactly like the show, except between “commercials,” they blasted music while the cast huddled. 

Jon was emotional and fired up—this was right after the Wisconsin state senator shooting. After the main part of the show, Jon lighten it up by congratulating his Lighting Director. It turned out that he had won the  Pedro Pascal lookalike contest over the weekend. (This part didn’t air, but lives on somewhere in Internet extras.)

John Mulaney was the guest. He did a bit about wrestling teenagers. I didn’t fully follow, but it was very “Jackass meets intellectual improv.” I will say the two John’s had a very good rapport with each other and we’re fun to just watch banter. 

Walking out at 7:15ish with a high that we did it—we finally saw The Daily Show. Afterward, we cabbed to the hotel and celebrated with dinner. Tired but triumphant.

There is more to this trip but I want to jump ahead to the other show taping (I will circle back on some other details later). 

Next day: Colbert. We had tickets to The Late Show taping at the Ed Sullivan Theater. Same drill—line up by 3:30, check-in, security, no phones. But this time, they told us we had a job: laugh. Be excited. Act like it’s the best thing you’ve ever seen. Honestly, I think I worked harder in that audience than I did in college group projects.

The guest didn’t show—Nate Bargatze. The upside is we got out early and snuck into a Broadway show next door. (More on that another time.)

Here’s what I learned: these shows involve a lot of hurry up and wait. You also have to bring your “entertaining human” A-game, which is a big ask if you’ve already had to sprint through LaGuardia and carb-load on airport pretzels. Honestly, one taping per trip is plenty.

Behind the scenes, both shows were packed with crew—cameras, cranes, lighting people, interns, someone filming vertically with a phone (probably TikTok), and someone Windexing the host’s desk like their life depended on it.

In the end, despite mechanical failures, cosmic interference, and being personally targeted by the universe last November—we made it. Alex and I saw The Daily Show and Colbert. If that’s not a redemption arc, I don’t know what is.


Crosswinds

So I wanted to do a little extra on this New York trip—and first, a quick shoutout to the hotel: we stayed at the Hotel Chelsea. This place is absolutely charming and full of character. Alex and I booked a suite (because we were sharing a room). It had a full kitchen—small, but New York big—and the whole place has this bohemian, slightly haunted vibe that I was very into. Apparently, some people still live there full-time because the building has been around for over a hundred years and is practically a cultural landmark (and rent controlled).

The hotel’s history is wild—artists, musicians, writers, ghosts (possibly), and now…us. I tried to lean into the spooky stories, but Alex made me dial it back because she was already having trouble sleeping and didn’t need me whispering “Nancy Spungen” at 2 a.m.

This part of the city was new to me, and honestly? I’d come back in a heartbeat.

We also had dinner at El Quijote, Spanish restaurant inside the hotel. Highly recommend the calamari. It’s the kind of place where you half expect Hemingway to be lurking in the corner, complaining about the wine.

The next morning, we hopped on the subway and headed downtown toward Greenwich Village. We made a stop at the Stonewall Inn Memorial and wandered through the area, soaking it all in. The weather was kind to us—it threatened rain (a little spitting) but never really delivered. It was overcast and cool, which meant no melting, so we counted that as a win. We made it down to Washington Square Park and just loitered a bit like locals. Bonus: there was a Frenchie sighting.

The thing about New York is, there’s a fantastic bakery on every corner, which is great because none of the shops open before 11. So, we adopted a strategy of walking, pastry, repeat. A little hydration, a little sugar, and on we went.

Then we made the very necessary pilgrimage to the Ghostbusters Headquarters, which is still a working fire station. We found that out when the fire truck came barreling in mid-tourist photo. We also may have located Taylor Swift’s building—we saw one with an absurd amount of security and decided that was it. No actual Taylor sightings, but we felt spiritually close.

All in all, I’d highly recommend getting out of Midtown and exploring some of these neighborhoods. Great shops, beautiful architecture, and a whole different energy.

Oh—and Alex had three celebrity sightings, all of which I responded to with, “Who?” Which is why she doesn’t take me to LA.