Blackbeard

He walked into the restaurant. 45 minutes late. My two girlfriends, seated on either side of me, gripped my arms in near unison. They audibly gasped. Or at least it felt audible.

Fuck. Me.

Let's rewind and let me tell you a little story about the first time I've ever been catfished.

I had really been trying to date. I asked people to set me up. I got a lot of the "you're so focused on your career you don't have time to worry about something as silly as your personal life!" But occasionally people pulled through. And even more occasionally, people really pulled through. But sometimes they pulled through in ways I never anticipated.

I'd been out with some good prospects recently. And then a girlfriend offered one up that gave me the excitement you feel when they unveil room service from under those silver domes. We were out to dinner, brainstorming men with whom we could set each other up when she exclaimed, "Wait…I have a good one for you!" She gave me his background. Good enough, I thought. At least he didn't work in private equity. She thought the age was right for me (old for most people, but I had in fact dated a few men on the precipice of AARP eligibility). He seemed ambitious enough. And when I say ambitious, I don't mean monetarily. I mean ambition in the sense that he could be a garbage man as long as he strives to be the best goddamn garbage man of the tri-state area. I digress. He sounded great.

She connected us by text and we started chatting. It took a little while to arrange an evening for our first date, but eventually we found a time that worked. In the run up to the date, he'd certainly seen what I looked like. I'm active enough on social media and had enough highly posed headshots in my google search results. In short, he knew what, and whom, he was walking into. I, however, had little to go on. The friend never sent me a picture, but I trusted her judgment.

In the 15 seconds it took him to walk from the doorway of the restaurant over to our table, I did an investigative rewind on the VCR of the past 30 days. Most times we FaceTimed, he'd been wearing sunglasses outdoors. On the rare occasions he was indoors sans eyewear, he'd been walking around his apartment and it really was kind of hard to get a good sense of what he looked like. In retrospect, the FaceTime sunglasses were perhaps less "cool guy" or "I'm old and want to avoid cataracts at all costs," and more "Witness Protection."

Now, I don't judge men solely on their appearance. Solely. But... He looked like he had been drawn from memory by someone who once saw a man. He also just wasn’t the person I had constructed in my mind. It wasn’t one thing I could point to; it was everything all at once. A feeling of complete betrayal by my own imagination. I've always believed in giving people the benefit of the doubt. Unfortunately, doubt tends to relish beating the shit out of hope with a tire iron. Friends kept warning me that it was important we not speak too much before meeting. I agreed. He even agreed and made the same point to me over and over again. But then he kept texting and calling and telling me, "I know I said we shouldn't speak too much before meeting but I like hearing your voice and I miss your face." If he had turned out to be my Prince Charming, all of this could have been spun to write the cutest wedding toast of all time. But unfortunately, for the duration of our courtship I was emotionally involved with a Midjourney rendering of a man who turned out to be one of those glitchy images with three fingers on a hand and no elbow rather than a well-executed rendering of a Howard Pyle.

It's hard for me to describe the man who walked into the restaurant that night. "Ana, I swear to you that man was a pirate with a peg leg," Sophia blurted when we got into the Uber. "THIS IS WHAT I'M SAYING!" I screamed back. He didn’t look like a pirate per se, and he did not have a peg leg to be very clear, but it was the ineffable energy he was giving. Something about him just screamed maritime and scurvy. I wouldn’t call it a visual lie so much as a tonal one. Everything about our digital connection suggested charm and ease and it so wasn’t like that in real life.

During the course of our virtual courtship, I'd gone through many stages. At first I was infatuated. He was funny, engaging, and seemed to really like me. Here's the problem: I have a horrible habit of absolutely despising men who seem to really like me. After two weeks I got the ick, hard. His full-time job seemed to be talking to me all day, everyday, every second of every day, and sharing every detail of what he was doing all day, every day, every second of all day every day. But I knew my pattern and was desperate to break it. Ana, just because a man shows genuine interest in you doesn't mean he's disgusting. So I tried with all my might to rattle the ick loose and actually succeeded. We kept talking. In terms of texting, he had range. From things like "just saw a cloud that made me think of you" to "I don't use AI, but I prompted it to write a short story about you. You tamed a dragon and then ghosted it." Then the ick came back with a mother fucking vengeance, and I was so desperate to ditch the impending first date. But I didn't really have a choice.

My first date with him also happened to coincide with the emergence of a few other prospects in my love life whom I was genuinely excited to continue seeing. The pirate sat at the tippity bottom of my suitor stack, but I knew it was the kind of bandaid I had to rip off—completely raw, unsealed skin unready to be exposed to the fresh cold air.

So we ate dinner. I sat down and couldn’t believe that I had spent so long talking to someone virtually, connecting with them even, and for it to feel so off in person. It felt less like a date and more like a live-action adaptation of a gross misunderstanding with the ghost of Long John Silver. Everything about the evening screamed ‘this is technically fine,’ but it so wasn’t fine as we sat through a vibe-less dinner that fell somewhere between jury duty and a team-building exercise. There simply wasn’t a spark as much as I wanted there to be. My imagination of who this guy was going to be was so completely divorced from what was sitting in front of me, which was sort of a poetic take on the role of technology in the age of modern dating.

We wrapped dinner faster than Captain Sully's emergency landing. Faster than Tom Hanks playing Captain Sully doing an emergency landing. I pretended to fall asleep on Sophia's shoulder. I turned to her, "Sophia, please take me home I'm expiring." He probably wasn't buying it, but I was too emotionally exhausted, overloaded, and disappointed to feign another minute.

Looking back, I feel like a Victorian widow who fell in love with a pen pal—only to meet him and discover he's more mustache than man. Or in this case, Calico Jack of the Venice canals.

A week later, Stella needed to get her groove back so I decided to take myself out on one of my classic solo dates. I started at Stafili, the wine bar in the Village, where I sat in the window on the most perfect spring New York day, and wrote in a way I hadn't in years. They needed my spot back by dinner time, so I made my way over to Bar Pitti where all I wanted was their crispy funghi, a piece of grilled fish, and the crispiest roast potatoes in all of Manhattan. I sat down, ordered a glass of wine, and pulled out my iPad to do some light writing by finger.

"Don't go on Hinge!" I heard the man say to the woman, who until two seconds ago I presumed was his girlfriend. I saw my window. "Do NOT go on Hinge," I said to her. "SEE? I told you!" he threw back. She asked why. I explained that all online dating was garbage and that she had to go meet people in the real world. "I don't go to bars though," she explained. “Just dinners and lounges with friends.” Ok, I thought, we operate in the world differently but it doesn't mean I can't help her. "So you need to go sit at restaurant bars alone. Take a book, take work, and men will just come talk to you. I met one of my exes that way. I've gotten too many dates to count that way. Trust me."

Then the man piped back in. "Stop helping her date other people!" I smiled. "Sorry," I shrugged.

She saw my materials: book, journal, iPad, pen. "Do you write books?"

I said yes, knowing it was kind of a white lie since I had yet to write a book that sat in any establishment. She asked some follow-up questions and I divulged that I had been working on my first book, since writing wasn't my full-time job, but was the thing I loved most in the world. I turned the conversation back away from me, which is where I prefer it. I asked him how they knew each other and how they ended up at Bar Pitti for dinner. The woman told me they'd dated on and off for three years and that it was super complicated. "I told him to go fuck himself, and he wouldn't stop chasing me. So now we're here. We haven't spoken in three months," she explained. I grinned. "Tell me everything."

She proceeded to tell me that she was Muslim, and he was Jewish, and that they could never possibly work out. I grinned again. This was an area I knew. Dating and Judaism? You must be kidding me. "Oh," I said, "so this is never gonna work out, guys. Are you religious?" I looked at him. "Very," he replied. "I'm half Israeli and my parents would never let me marry her." "I get it," I replied, "my parents have a clause in their will about us marrying non-Jews." He looked relieved in a finally-someone-understands-my-plight kind of way. I looked at her. "Are you religious?" "Yes," she replied. "I have a very traditional family." I looked at them and I said, "I wish you the best of luck. This is never gonna work out."

Naturally, we kept talking.

"Tell us about your love life! Are you dating anyone?" she asked me. "Loaded question," I replied. "It must be easy for you in New York though. Everyone is Jewish." "Well sure," I replied, "but you have to remember we are still only 2% of the global population on a good day."

Naturally, I told them about the pirate, the subject of my writing for the evening, and then dipped into the other facets of my love life, which were far too layered, chaotic, and legally ambiguous for the written word at this point in time. But what really interested me was their dynamic: a three-year on-and-off saga with a religious roadblock that made Romeo and Juliet’s drama look like getting picked last in dodgeball.

"Ok but can I ask, why did you guys stay together for three years, if you knew you couldn't end up together?"

"He's a classic chaser," she explained. Hah, I know that story well, I thought.

He piped in. "I'm not a chaser! I'm just a 'chase her' to be honest. I just really love her. So I chase when I love and I don't usually love so like, you know what I mean? I didn't have a choice. I love her so I had to chase her."

"How would your parents feel about you marrying someone who isn't Jewish?" I asked him.

"No, it's not an option. Like I grew up speaking Hebrew."

"So then why do you keep coming back to her if you can't be with her? Why haven't you dated anyone else in between if you've been on and off for so long?" I asked. She looked at me with a knowing glance. "He has commitment issues." He shrugged in mild agreement.

"Ok, let me explain what I think is going on,” I said with far too much confidence. “Sure you love her. I believe that. But you also have commitment issues. Most men do. You keep coming back to her because yes, you love her, but you also know you'll never have to commit to her because it's simply not an option."

"But I WOULD marry her!!" he protested.

"Sure, but you can't. And that's my point," I argued back.

They turned the conversation back to me, and my personal life, unfortunately. But it did give me the opportunity to test out some of my pirate content on two perfect strangers. I told them about the other dates in between—the ones that lasted an hour and the ones that had dragged on for years. It was cathartic telling two anonymous characters about my messy love life in a way where they could never identify any of the characters nor ever know my own name. I finished sharing and realized I had finished my meal and my glass of Gavi.

"Ok, I'm going to pack it in and go to bed, but first let me tell you how this is going to end up. Option one, you guys break up and really never speak ever again. Option two (and I looked at her), you are going to have to convert. I'm sorry I'm not saying this to him but unfortunately you will have to be Jewish if you want to be with him. Period, end of story. With that, I wish you both the best of luck. Godspeed."

I walked back through the Village to my apartment. I felt for them, but I also have very strong, very controversial views on intermarriage and was kind of rooting for them not to work out. We need more Jews on this planet and I don't even really believe in conversion. Sue me. But my little audience of two at Bar Pitti that night gave me a little confidence. Confidence that my content was still decent, that I was still just a little bit funny and light, and somehow confidence that the pirate was not the best it could ever get for me.

All in all, perhaps my only consolation is that someday, when I'm married to someone non-icky, with a hobby aside from me, and maybe even physically vaguely symmetrical, I'll retell this story to remind myself of what I survived to get there. Because sometimes "hot and funny" is in fact just code for "looks like he sells cursed jewelry at a Renaissance fair with the sex appeal and seductive prowess of a corresponding court jester named Triboulet." And I beg of you to google Triboulet.