I think it was the movie Breakfast at Tiffany’s that started Olivia’s obsession with New York City. Even as a little girl she had sophisticated taste, preferring Audrey Hepburn over Miley Cyrus. Whatever sparked it, my daughter spent her entire childhood telling her father and me that she was going to live in New York City one day. And when Liv says she’s going to do something you’d be wise to get the hell out of her way and just watch the magic.
In 2015, when she turned 16 years old I took Olivia to New York on her first Ladycation. I had never seen the city myself, so I decided we’d explore it together. As you know, I take my Ladycations very seriously, so I planned the shit out of this Little Ladycation. We spent two nights in a fancy hotel room overlooking Times Square (then two nights in Brooklyn, staying with my stepsister), enjoyed her birthday dinner at a swanky steakhouse, celebrated our liberties at the Statue of Liberty, soaked in the view from the top of the Empire State Building, clowned around the Natural History Museum, and paid our respects to musical legend John Lennon at Strawberry Fields in Central Park. But the highlight was Wicked.
Olivia had wanted to see a Broadway show for almost as long as she’d wanted to live in New York. I did some research and spoke to my stepsisters, both of whom lived in NYC at the time, and decided to take her to Wicked. But, I didn’t just want to take her to the show. It was her Sweet 16, I wanted to do it right. I wanted front row center! I didn’t tell Olivia we’d have the best seats in the house. I told her the seats were very expensive (not a lie), and that we’d be near the back of the balcony. She said, “That’s okay, Mom, I’m just happy we get to go. I don’t care where we sit.” When we arrived at the theater and were being led closer to the stage Olivia looked at me, confused. “Oh, by the way, I lied. We’re front row, center. Happy Birthday.” She scolded me, but the smile creeping up on her face was all I needed to see to make the expensive charade worth it.
Both of us fell in love with Broadway that night. First of all, Wicked is spectacular. Such a great story, beautiful, with fun music, and the actors were fantastic and obscenely talented. We laughed, we cried, we cheered, we loved it. After the show we stood by the stage doors and waited for the actors to come out and sign autographs. We’d had such a wonderful night! Of course, nothing is perfect, so I accidentally led us about 8 blocks in the wrong direction (in heels) trying to find our hotel, despite Olivia telling me we were going the wrong way. She wanted to punch me in the face, but we laughed anyway. I’m fairly certain that trip cemented Olivia’s desire to live in New York City.
And so, when Olivia graduated college, after we returned from our epic European Ladycation, she and Carey loaded up a U-Haul and did exactly what she said she was going to do more than a decade earlier: they moved to New York City. Like I said, stay out of my girl’s way!
Having a daughter living in NYC is pretty great (fucking terrifying, but also great). What better place to be forced to visit than a city with endless things to see and do?! Thank god she didn’t move to North Dakota. So, a few months after she’d settled in, I hopped into Ruth Bader Ginsburg, my trusty Volkswagen, and road tripped to New York for a long weekend with my Number One gal! I got an early start so we wouldn’t be late for our first activity of the weekend, something that allowed me to check another item off my Bucket List: attending a live taping of The Late Show with Stephen Colbert!
Oh, how I adore Stephen Colbert! I’ve been a super-fan for more than a decade, and was so excited when he took over for the legendary David Letterman. In fact, when Olivia and I went to New York for her 16th birthday it was during the interval between Dave and Stephen. I was so overjoyed when I got tickets I almost ran around my office screaming like a teenage girl at a Harry Styles concert.
I arrived at Olivia’s apartment in the early afternoon, and after she gave me the tour of her adorable little pad, we got ready to head to Midtown to see Stephen, me grabbing a hot dog from a vendor on the way, cause I was famished. We were giddy as we waited in line. We received wristbands and were shuffled inside the lobby, and crammed in like sardines. It got rather stuffy, all pressed together and masked, but it was so worth it. When they opened the doors and we walked into the historic Ed Sullivan Theater I was in absolute awe. When Stephen came out I practically swooned.
Holy charisma, Batman. He was as charming, and warm, and funny, and beautiful as I knew he would be as he greeted the audience and interacted with his crew. When there were technical issues setting up for the musical guest Stephen came out, jumped up on his desk, and started taking audience questions. He didn’t have to do that, he could have sent his warmup comedian back out, or just made us sit there and wait, but he’s the real deal, folks. It was incredible. If his beautiful wife Evie had appeared I may have asked if they’d be interested in becoming a thruple.
We watched interviews with Marie Yovanovitch, former U.S. Ambassador to Ukraine. This was shortly after Putin invaded Ukraine, and she came wearing her “Fuck Putin” bracelet, something she passes out to people who visit her office, which is just such a boss move. Then we saw Aidy Bryant from Saturday Night Live. As one would expect, she was hilarious, and though I didn’t know who she was when I arrived, I was a fan when I left.
Not ready to call it a night after the show, and me still hungry from consuming nothing but a street vendor hot dog all day, we stopped at Serafina for dinner. An Italian restaurant near the theater, Serafina serves Italian cuisine that’s better than the Olive Garden, but not by much. We enjoyed ourselves anyway, having a couple of cocktails and talking about Stephen’s amazingness. I loved that she, too, was fan-girling over my man, Colbert.
My Little Ladycation was off to a phenomenal start, and we still had two more full days of fun! We hopped on the subway to head back uptown to Liv’s apartment for the night. Between getting up at the ass-crack of dawn, the long drive, and the late hour, I was exhausted. I was looking forward to a good night’s sleep to prepare for the remainder of our mother-daughter weekend.
Thanks for reading! Stop by next week to follow along as I go into history nerd mode as we explore more of The Big Apple! And don’t forget to subscribe to Ladycations to stay up to date on the latest travel tips, tricks and tales! Until then, stay chill and keep hiking, my friends!