Did You Cross The Ocean to Chase Your Dream, Or ...?
Share

This letter is part of Nina's epistolary blog 'Nina's Diary', where she shares letters with her inner circle of close girlfriends. She overthinks films, books, and heritage sites to make sense of life.
New York, October 1st, 1958
Dearest Nina,
My last letter might not have reached you yet, but I couldn't wait for your reply before writing again—you’ve been on my mind all day.
This morning, on my way to an audition on Broadway (don't ask how it went; I had barely five minutes to play a score I spent a month practicing, along with a hundred other, far more talented candidates), I found myself walking past the Roseland building*—or rather, the parking lot that replaced it. Did you know Roseland was torn down two years ago?
Ever since you and I stopped going to Charlie's**, I've barely set foot on this side of Manhattan. Standing before that car park, with its cold, flat asphalt and rows of empty cars, it felt miles away from Roseland's bright neon lights and those packed, noisy ballrooms.
Do you remember how we never failed to rush over to Charlie's Tavern the second your shift ended? Early enough—actually, we were shameless, showing up way too early—to stake out two prime spots at the bar, complete with stools. Joe*** used to throw lethal glances at us and our never-ending drinks from behind the counter. If looks could kill! We could only afford two pink squirrels, and we sipped them at the slowest possible pace. Bless him, he never said a word.
You always showed up while I was chasing a gig, hoping to bump into the right contractor at Charlie's. Oh, the excruciating conversations we had to endure with the least handsome men in the room! I’ll never understand why those are always the first ones to approach two women sitting alone. What an absolute mystery!
Everything changed the night Millie joined us, when she landed me that wedding gig and my very first piano student. How distant those days feel now. Charlie's will always hold a special place in my heart—it was where we shared our most embarrassing laughs and perfected the art of scaring off unwanted suitors.
I'm holding a photo of the bar, which I’ve enclosed in this letter. I was told it was taken back in 1947. Joe looks so much younger here than I remember, doesn't he?
I didn't realize it then, but everything was so full of life right up until we stopped going. I never had the nerve to ask you back then, but I suppose I have the distance between us to thank for my bravery now. Two years ago, right in the middle of a wonderful night at the bar, you suddenly insisted on leaving and never said why. What I never told you is that I saw Him walk through the door. I respected your silence that night, but I always knew we never went back because of Him—and right after that evening, you started talking about leaving New York.
So I have to ask you, Nina: did you cross the ocean to chase your dream, or were you just trying to escape Him?
With love,
Your forever friend,
Billie
(*) The Roseland Building on 7th Avenue was a legendary jazz hub that housed iconic musician hangouts like Charlie's Tavern and Birdland, before the building was torn down in 1956.
(**) Opened in the 1940s in Midtown Manhattan, Charlie's Tavern was owned by Charlie Jacobs and famously managed by Joe Helbock, serving as the ultimate "living room" where legendary jazz musicians, publishers, and songwriters routinely gathered to book gigs, trade gossip, and find work.
(***) Joe Helbock was a legendary jazz-scene host and former operator of "The Joint" on 52nd Street, whose immense popularity and charisma behind the bar transformed Charlie's Tavern into the premier gathering spot for New York's elite musicians.
💌Next: Read Millie's Letter to Nina - Breakfast at Tiffany's, What Shook Me So
![]()
This photograph of Charlie's Tavern is part of Billie's Iconic New York Polaroid Collection: 12 historical snapshots printed on real Instax Square film.