#BadDateFiles: The Unsolicited Second-Date Mix CD
“Harry” and I matched on the Hinge dating app, which at the time indicated that we were connected within a few degrees of mutual Facebook friends. He was friendly, upbeat, and gainfully employed in an industry closely related to my own. For our first date, he suggested a casual yet classy wine bar near Union Square. After a few encouraging text exchanges, I was looking forward to meeting him.
It was early spring, and over the course of the afternoon on the day of our date, the proverbial “April showers” had intensified to a steady, chilly downpour. Surge pricing was in full effect and there wasn’t an empty cab to be found, so I took the 6 train downtown. The walk from the Union Square stop to the bar was just long enough to make my shoes squish and my hair frizz under my cheap drugstore umbrella.
Harry greeted me warmly and, to his credit, seemed unbothered by my waterlogged appearance. We shared a bottle of red wine, hummus and a cheese plate. It didn’t take long for the conversation to land on the topic of music. It turned out he was a classically trained pianist and a lifelong music lover who clearly shared my own appreciation for live music. When I mentioned that one of my all-time favorite artists is folksy acoustic singer-songwriter Stephen Kellogg, Harry lit up — even though he’d never heard of Stephen.
“Are you a fan of Glen Phillips?” he asked me. I didn’t know Glen, but I did know of his band, Toad the Wet Sprocket, from the Friends TV soundtrack and a Counting Crows show I’d been to years before where they were the opener.
“Glen’s one of my favorites. You’re going to love him. I’ll burn you a CD.”
For our second date, I invited Harry to join me at a show I already had tickets for at City Winery. It was a “rehearsal” for a benefit concert taking place the following evening at Carnegie Hall to honor legendary songwriter Jimmy Webb. The real show would feature big-name acts including Graham Nash, Art Garfunkel and Hanson. The rehearsal show, on the other hand, made no such promises. I bought the tickets hoping a headliner might make an appearance. Spoiler alert: they didn’t — but it was still a good concert.
Based on our first date, I figured that Harry appreciated music enough to enjoy the gig, even though Jimmy Webb’s heyday had been decades before our time. And to his credit (again), he was a really good sport about tagging along with me.
He also brought me the promised Glen Phillips mix CD.
I know I should have appreciated this gesture, just like I should have appreciated the “surprise” glasses of dessert wine he ordered for us while I was in the bathroom. But when he walked me to the subway and went in for the goodnight kiss, I didn’t feel even a hint of a spark.
When I got home, I put on the mix CD (If Harry is one of the few men in modern-day NYC who still burns CDs, then I’m one of the few women here who still owns a CD player). Maybe I would love Glen Phillips. Maybe there was a song on this CD that would touch my heart, speak to my soul, or, at the very least, hint at the remote possibility of a deeper connection between Harry and me.
There was not.
I wasn’t eager to see him again, but I couldn’t quite put my finger on why. Harry was intelligent, cute, successful, impeccably well-mannered, cultured, kind, and above all else enthusiastic. He kept up a steady stream of cheerful, attentive text messages. He held doors and bought drinks. He smiled. And he’d gone to the trouble to bring me a personalized gift after just one date! Meanwhile, I can’t even decide whether I like a new purse until I’ve been out with it four or five times, let alone a prospective partner.
And that was when it clicked why Harry and I hadn’t clicked. Rather than letting us establish a natural and genuine connection, I felt like he was putting on a performance to try and impress me — but without bothering to figure out what actually would impress me. I didn’t like the dessert wine (too sweet) and I didn’t like Glen Phillips (too bland).
Harry thought he was scoring points for making romantic gestures, and he expected me to be delighted with him for it. But to me, they felt like tactics from a manual on “How to Make Girls Like You in Five Fast & Easy Steps!” I’m not ready for romantic gestures on date two; I’m still making sure you’re not the kind of guy who talks in movie theaters or refers to women as “females” in writing (I’ve dated both those guys, and I do not need to go there again).
In the end, it was Harry who politely gave me the brush-off a few days after we parted ways on Varick Street. But he was a truly nice guy, and I’m sure the right woman for him is out there.
I predict he will find her front row center at a Toad the Wet Sprocket concert.
