My First Real Date Post Marriage

Well that was NOT what I expected...

Two years and eight months (give or take) after my husband and I split, plus 5 months after the I-should've-known-better-than-to-jump-into-a-new-relationship and I parted ways, I went on my first proper setup date, courtesy of a close friend. He was a TV-personality type (save the eye-roll), about my age, newly single-ish (though the details of his divorce are questionable), and he had just moved back home to NYC from LA. We talked over text for about a week before deciding to go for drinks, maybe dinner, in the lobby of The Mercer Hotel. He seemed nice enough, but for the occasional sexual innuendo that I chose to ignore, given we'd never met. 

Leading up to the date, I was so nervous. Nerves that reached right into my core. I hadn't been on a date since, well, forever. In fact, I'm not sure I'd ever been on a proper date. One in which you dress up to meet a virtual (if not actual) stranger. I know this is hard to believe, given I've been married and divorced, but I was 24 when I met my ex-husband, and we'd been together for almost ten years before we separated. Then, true to fashion, I jumped right into the next thing for another couple of years. You do the math, but the short and long of it is I had never, until that night, gone on a date to meet a stranger for drinks. But there I was, in my mid-thirties, doing just that. 

We had a few flirty text exchanges the day of. At one point, he asked if instead of meeting at 7p, we could meet at 5p to see "his friend Pharrell" record a taping for some show. Ummm yes! But wait, no. I couldn't make it in time. I was uptown, in sneakers, and had hours of primping. Though I didn't say all that, I only said I couldn't make it until 6:30. He replied, no problem, let's keep it at 7p. See you soon. 

So I dove head first into preparing for the date. I had big plans: a blowout followed by The Face Gym (yes, seriously, it's a gym for your face), and outfit options were reviewed by a committee. Mentally, I played the "what if?" and "could this be the one?" game. During those early days of dating, it all meant so much. Every date was a potential future mate. I've learned a lot since then. My advice to friends is to date everyone. Literally. And date "in threes," meaning have three guys in the mix at once, so there is never too much pressure on the one you're really into. And most importantly, have fun! The stakes are so low at first until someone is truly worth your time, the blowout, and the effort. But no one had told me this, so I went all out on this one.

I tried on the final ensemble an hour before pick up: black jeans, heel boots, and a black bodysuit. I looked at myself in the mirror. Sideways, both ways. I took photos with two jacket options and sent them to the committee, captioned: this or this? Decidedly it was the cropped fur. I looked in the mirror for the last time. Sideways, both ways.

Sam:

There is a gift waiting for you in the car.

CC:

Coming!

I felt too done, but apparently, a car was outside, so I finished my tequila and headed downstairs. At that moment, I wished I had taken him up on the offer to see Pharrell at 5p in my jeans and a ponytail. Undone and a little messy is always best. Why did I say no to that? I'm always so spontaneous. Why did I need to "look perfect?" Overdressed and underwhelmed, it all felt so forced. 

Stepping into the night, the day had been replaced by a cold, damp mist. There he was, leaning against the hood. I saw him for the first time, haloed by the headlights. Sam. Tall, with dark brown hair shaved close to his head, a bit of facial hair, and a square jaw. Baggy jeans and Jordans… a bit of a man-child. He looked up. Ok. Not the best, not the worst.  

Turns out he was the gift waiting in the car. Clearly not his first date, and if it hadn't been mine, I probably would have found it cute, charming even. But it was, so instead, it made me incredibly uneasy. I wished it was over already. What do people even talk about on dates? 

We pulled up to the Mercer Hotel. Still very newly post-covid, they offered us a seat outside under a heat lamp, but it was cold, so we asked to be seated inside on a sofa. 

Awkwardly settling in, I shifted to find a way to sit comfortably, gracefully, and still look at him. I perched at the edge so I could turn to the side to face him. I was unsettled while he was entirely at ease. He dropped in, relaxed, and hung back but kept his jacket on. He smelled good, and he looked good. I was starting to feel much better about the whole thing… until the conversation began. 

We remained on the surface. I couldn't connect. He talked about his father's wealth as if it were a flex (note to all the guys and gals out there… this is NOT sexy) and his grandfather's journalistic accomplishments, which were entirely something. Admittedly, if it had been fifty years prior, I would have wanted to date his grandfather. And then he talked about himself ad nauseam. The flood in his apartment. His sneaker collection. How his sneaker collection was ruined in the flood. The Jordans he bought to make himself feel better about the flood (note: they were cool). Then he got up to call his lawyer to follow up on the email he had just sent about the flood. I perked up when he returned and shifted the topic to the new show he was hosting... but then he pivoted to sports and back to the flood. In what was clearly a last effort to sweep me off my feet after getting to know me so well, he quoted Diddy. And it was from "I'll Be Missing You." Words most women only dream of hearing… swoon.  

As the evening passed, we realized he had dated one of my best friends in high school and knew her family well. He shrugged at the coincidence; meanwhile, I was floored. (Since then, I've learned that this is entirely normal in the land of dating. Everyone has dated everyone.) Then, the big moment came when he asked me a question! The first one of the night. Totally caught off guard, I felt like a deer in headlights stumbling over myself to answer. He seemed surprised to find out that I was a mom; maybe it made him uncomfortable. I'll never know. Arms crossed, he bounced his knee and remained aloof the rest of the night. 

To be fair, I was not my best self. My effortlessness vanished and was replaced by utter awkwardness. I became some expectant, wanting girl, hoping for a future with someone I didn't even like. Wide eyes, faux-flood enthusiasm, and feigned interest. It all felt so performative. 

We finished our dinner and left. Quickly hugging goodbye outside of the hotel, I slipped into my Uber. Finally, alone. As uncomfortable as it was, I was proud of myself. I let out a deep sigh. Something inside me opened; with one down and many to go, I was headed in the right direction. There and then, I decided that I was officially dating… by proper invitation only. I also decided I'd never wait on a guy to determine if he likes me. Nope. It was going to be mutual. Resolute in this, I knew if I held to those values, I would someday be exactly where I hoped to be at exactly the right time. 

Over drinks the following night, I told the whole "first date" story to a girlfriend. Turns out, in her twenties, she used to date him too! Then she retracted and said, actually, we just slept together on occasion. If that doesn't sum up dating in New York City, I'm not sure what does. Anyway, who's to say what qualifies as dating? I sure don't know. I've been married and divorced, and I still don't know. He was a nice enough guy, just not my guy, nor hers. We took a photo of the two of us together and texted it to him. He hearted it ❤️

Photo: Vogue Australia