The Most Traumatic Two-Date, One Week Adventure of My Life

Energy. I’ve been using this word a ton lately when it comes to dating. It’s the abstract fourth category of matching with someone that arguably means more than all of the others combined (if we’re using personality, looks, and timing as the other three).

via (cecile_hoodie)

The tricky piece with energy — is that when it translates to text, it’s very difficult to track or keep that going. That’s also why dating apps and I have never been a great fit, no matter how many “Super-Likes” I threw in (I eventually realized my “NJ -> MI -> SF -> NYC” dating app bio reads more like a college admissions tour than a display of my many worldly travels). You can’t swipe based on energy, and that’s always been the issue for me.

…and of course, getting off dating apps & attempting to only date in the real world has led to an average of 1.5 dates every three months, which is ironic considering I run a fairly popular dating show here in New York City. So yes, I battle every day — just like all of us — with whether I should DM the 🤓, (the most subtle “I’m into you” passively to my ex-college crush posting wedding pics or whether I should just “watch her story).” And also just like the rest of you, I still cannot figure out how the second I’m into someone…it ends. Before. I. Can. Even. Fill. In. My. Jewish. Mother.

After a brief fling with a nice gal from Kansas, I’ve been laying lowThat is, until I met the plumber.

THE ENERGY, THE EDGE, and THE VIBES. CAN’T YOU SENSE HOW PUMPED I WAS ABOUT HER?! While thinking to myself, “Carrie Bradshaw would be proud of me.” We exchanged IG’s and a nice kiss on the cheek, I complimented her set (…a story for another day, men don’t compliment women enough), and ended the conversation strong: “I’d love to go out with you sometime.” Direct. Bold. Confident. Tequila-enhanced. The perfect way to end our first encounter.

What followed was the most topsy-turvy, up-at-dawn, morning walks with Marvin Gaye-blaring romantic week of my New York City life.

As I boarded my flight to California, I noticed two highly specific notifications: a 4am IG follow from the plumber (after 1 AM, you know it’s a great sign) and a text. “Hi…I have a friend for the show.

My six-hour flight originally planned to consist of rest, Frank Ocean’s Blonde, and two overpriced roasted turkey sandwiches… turned into my greatest texting feat to date.

Time stood still. The plane hovered over the clouds as we sent hundreds of texts to each other over the course of the flight. This was the type of thread I love, the type where it’s cool to send 3–4 texts in a row, even if your entire screen looks blue. We discovered our moms had the same first name, “Lisa.” My most beloved HBO shows, Sex & The City, Entourage, and Curb, were her favorites, too. We expressed interest in breaking Jewish tradition for a tattoo. We even discussed our shared disdain for the so-called “mind games of texting” today.

This was not just a texting conversation; it was a Ryan Gosling-Emma Stone flick on steroids. It was just so raw, so real, as if she was sitting in the empty seat next to me on the flight. So real, in fact, she hit me with the:

“Why do I feel like I like you. I don’t even know you.”

Mic drop. I feel the same! Should I text her that? Okay, I’m about to.

“Same here :)”

I decided there was way too much synergy here to wait an extra day for our date on Tuesday. My flight was landing at 10pm tonight. I didn’t want to wait-after all, this fling was throwing out the rules.

“Look ‘rules will tell me to wait until Tuesday’ but F*** the rules. Can I see you tonight?

“What time do you land?”



“Um, yes.”

I dropped my bags off, debated the “should I shower?” question for thirty minutes with my roommate (opted in for the Biore Facewash #sponsored) and then scooped right over to the empty bar venue.

When we decided to sit next to each other instead of across from each other on the suede tan seat, I knew the texting vibe would translate to the in-person vibe.

The date immediately had it — we drank tequila, I played with her pink necklace, we talked about going to yoga together, and then the first make-out happened. From all of the texting over the past few days, it already had that 4th date “Can we bring our friends out with each other?” vibe. Most importantly, I could see myself inviting her to yoga. And even more important than that, she had the edge I longed for.

After the date, the shenanigans continued at my place with a chill sesh of mostly talking until 4am. Miraculously, I still made it to my 8am meeting on time.

The texting energy was everything you could ask for after a successful first date. She shared the great impression I made on her with her friends. We set up date #2 for the same night. The three-day bender with no sleep could not stop me from wanting to see her again — this time, with the finest Balsamic flat breads & wine this side of Murray Hill.

Again, we sat at the bar, schmoozed, vibed, and (gasp) held hands. Date #2 (n my eyes) was a massive success despite mutually opting out of the late-night shenanigans so we could both get some sleep. Before the Uber departure (in what later may have been the ultimate red flag), I threw in my dose of PDA. “I’ll have to warm up to the PDA,” she said. Then…she left.

From here, my whole world turned upside down. Wednesday saw a few scattered texts (mostly me throwing in inside jokes to spark the convo). Again, she and I decided on Day #1 we weren’t going to play by the rules of the game, so I assumed texting first would be okay. A few haphazard responses with ZERO emojis from her side told me something was up.

Thursday saw not a single text exchanged. Thursday also saw three panic attacks, 10 separate moments clicking into our texting thread, and at least two occasions of typing out a “hi!” only to backspace moments later.

Friday…I decided to text her first again. I just had to. After all, how could anything be astray?

I fired off a semi-aggressive, but flirtatious text: “my mom is so happy I went out with a Jewish girl…” Not my greatest text in the world, and ironic considering I’m not really in the “she-has-to-be-Jewish” camp for dating. Regardless, I sent it. her response was scattered and confusing with a few “haha’s” was “she got her wish.”

The vibe was off. Our vibe was off. The nonstop flirty texting. The “I like you,” the “baby, baby,” the “what would we do in bed together now?” from her felt like texts from centuries ago — yet they were entering my inbox less than 48 hours ago.

The short exchange ended with her wishing me good luck on the show; my “Hola Hola” after the show, received a passive (albeit disappointing) response “Sup.” It was clear we were not linking up tonight, and seeing her again would be unlikely.

…and so here we are. Dissociation. Confusion. Sadness. A lot of sadness.

Why is it that the second I really pursued her, she pulled away? Why is it that the “mind games BS” we excitedly decided to not follow the second my flight landed turned into the “mind games BS?”

Over the weekend, the monologue in my head over the weekend on how to react complicated everything even more.

I want to call her — should I? I just don’t really understand how this is happening. Our physical, emotional, and intellectual connection was so there. We talked about hanging out consistently. We plotted a Salsa night at the Playboy Club. Even Yoga! UGH! Classic New York. Wait for a cool girl. Vibe with said cool girl. Then she’s gone. JUST. LIKE. THAT.

The saga did not end there, unfortunately. I was hit with multiple passive Snapchats — yes, I actually re-downloaded Snapchat after a two-year hiatus to multi-platform our communication. And yes, I did reply to most of her snaps with the glasses emoji I discussed above (no, they were not answered back).

I decided, at 11pm, I must move on. That lasted until about 5am, when I texted her showing I had not in fact moved on yet.

After almost 10 panic attacks over leaving the city for Rosh Hashana dinner, I finally did it. No, I didn’t text her. I decided I wanted to text her, at least one more time, like a “hail mary” in football: it’s unlikely you’ll win the game, but the game hasn’t officially ended, so you take the leap in hopes that something will change.

“See you this week? Or Rosh Hashanah goals won’t align with that?”

Funny. Direct. On-brand.

“Haha Yas we can hang”

Weds?!” (Yes, I figured it would be slightly cooler not to type out the full Wednesday.)

“I might have plans can I text you tomorrow?”



The next day: Nothing.

Ballgame. Sadly.

Closure is a tricky chain of events in dating today. Rather than receive a full text from her on the multiple reasons for the pull away, I’m now left wondering “what if.” What if I opted for the pepperoni flatbread instead of the Balsamic? What if I never sent the text about the Jewish mother? What if I really was “a lot of person” and she realized I’m just too extra to handle at this early juncture? What if Salsa dancing at the Playboy club happened on date #1 instead of the nonexistent date #4?

The optimist in me is saying she pulled away when she realized she actually might end up liking me (after all, this was a direct quote in our honeymoon texting phase anyway). The pessimist in me, well, is continuing to say “man, your overthinking and neuroticism caused this. Too much too soon. Did Cali teach you anything about chilling?”

Well, forward we march. Contemplate we shall. And yes, continue to look out into the Empire State Building drinking overpriced Trader Joe’s Cabernet, longingly curious on the whereabouts of the amazing future bae I have yet to meet.


These UpDates from UpDating will happen more regularly chronicling the trials & tribulations of dating, life, and everything in between right here in New York. Yes, Date/Able podcast did call me the male Carrie Bradshaw once. And yes, oh yes, will I get back out there tomorrow and finally ask for digits from the cute Starbucks barista always giving me a venti Chai when I ask for grande. And most importantly, yes, don’t wait too long to buy your ticket to UpDating. It’s more fun than my dating life, trust me.

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