When he asked me to go ice skating at Rockefeller Center for our fourth date, I was thrilled. It’s a little known fact that should be more publicized: I adore an ice skating date. From strapping on skates to holding hands.  From daring each other to skate faster to dodging little kids. From cold, sore feet to hot chocolate. Ice skating really has all the makings of a perfect date: fun, romantic, revealing (does he try to make you fall or save you from falling?).

Though it was our fourth date, I still wasn’t entirely sure how I felt about this guy. It certainly felt like we were still getting to know each other. He was a little reserved, a little quiet, a little serious. But he was also very cute, very intelligent, and I saw the possibility for very fun if I could just get him out of his shell. I was also impressed he’d picked up my hint. When he asked if I was into any sports I replied, “Bowling and speed skating,” cutely suggesting date ideas.  “He must like me if he’s inviting me ice skating!” I thought, “Yay!” We made our date for Saturday night.

Saturday night, I emerged from the subway station to find the streets a mad scene. It was a Saturday night in December, why the hell was I surprised? Everyone and their entire family was in town to see the Rockefeller tree and the 5th Avenue holiday decorations. Oh yeah, and go ice skating! I’m no stranger to crowds, I’m often in Times Square when all the Broadway shows let out and I’ve recently been commuting to midtown, but this was the most densely packed place I’ve ever seen.

It should have taken me 5 minutes to get to my date but in the cattle-like crowd it took 15. When I finally found him, he had the same look on his face as me. How did we think this was a good idea?? So we got the hell out of there. Bryant Park was only 8 blocks away- they have and ice rink but no world-famous Christmas tree. We figured we’d try our luck there.

I lead the way down 5th Avenue to Bryant Park. I also led the way in conversation.  Something felt a little weird. Had he been demoralized by our Rockefeller failure? Overwhelmed by the crowd? I felt I was struggling to make this fun and was flailing. That’s never a feeling you want to have with someone.

We made it to Bryant Park and of course there was a line. It wasn’t long but he was clearly not into waiting. “It won’t be bad,” I said, “Did you ever play games on road trips to pass the time? We can come up with some to play in line.” Yes folks, that’s the level we were at. His contributions to conversations were so lacking I felt the need to suggest playing “I-Spy”. Look at me! I’m peppy and adorable and fun! I can get you out of this weird mood or whatever it is!

Did I ask him if something was wrong? Yes, yes I did. Did he give me any kind of real answer? No, no he did not. We continued waiting in the line.

And you’ll have to wait until tomorrow to get the rest of this story! Spoiler Alert: it’s in the running for worst date I’ve ever been on!

Click here for Part 2