The Curse of the 18-Hour First Date

I'm the joke... I've been cursed. I've been damned—not with bad dates, but with good ones that never end. Like a rom-com stuck on repeat, my love life is an endless loop of 18-hour romances that begin with possibility and end in predictable silence. And before you whisper behind a block of blue light, “Girl, it’s called a one-night stand,” let me stop you right there. It’s really not. Really, not at all.

One-night stands are sexy and impromptu. It’s meeting a stranger in the backyard of Rocka Rolla one night and thinking to yourself, you don’t hate Murray Hill as much as you think you do. The 18-hour first date consists of shameful swiping and cringe-filled banter, with a “We’ve detected potentially inappropriate language. Do any of the messages above bother you?” pop-up eventually. The 18-hour first date has a lead-up of internet stalking and scenario conjuring. By the time the date rolls around, I’ve already invented him.

I find myself stuck in a pattern of staying on first dates way longer (like significantly way longer) than necessary, but I’m always having a good time. Maybe I’m one of those rare people who can always have fun on first dates, especially backed up by my 20 mg Lexapro prescription. (Yeah, I seriously doubt that.)

When you hear about your friend having an 18-hour-long first date, you assume she must’ve met the love of her life. Who has that long of a first date with any other guy? (Ummmm, me if you couldn’t tell). I have a knack for having lovely first dates that never go anywhere. 

Is it my people-pleasing nature? My struggles with abandonment? My fear of disappointing others? My wishful thinking? Am I simply lonely and enjoying the company of a “stranger”? Is it not my fault in the slightest and entirely on the man every time? (HA YOU WISH! Well, most of the time, it’s a man’s, but in this case, I’m afraid not). I fear this is my hamartia on my journey to love. 

To provide a better picture of how these dates go, here’s a typical timeline:

7:30 PM: Awkward small talk about what we do for work begins over menus 

8:30 PM: “You’re from Iowa? Hold on, let me get out my map. I’m not sure where that is.”

9:30 PM: *Existential contemplation as we sit in a Bushwick dive*

10:30 PM: Still at said dive bar with a dash of “I’m having the best time” on the side 

11:30 PM: “Can I walk you up?” as he stands outside my door after walking me home

12:30 AM: Pouring Brita-filtered water into two glasses for post-sex parchedness 

1:30 AM: Quiet giggles and drowsy kisses

*sleeping shhh*

9:30 AM: *My brain thinking, “holy shit,” as he asks my favorite coffee shop*

10:30 AM: Vanilla chai burns my tongue as small talk dwindles over croissants 

11:30 AM: Closing my front door after he kisses my cheek and pinches my lower back  

12:30 PM: Ping! “I had a lot of fun last night :) When can I see you again?”

1:30 PM: *I hope he texts me back* OR *I never want to see him again*

(Also, side note: before you begin to remark, these seem like drunk actions you will find that you are indeed wrong. A cool trick of mine: I accomplish these 18-hour first dates completely sober, too!)

See? It always follows the same script. The settings may change—Bushwick bars, dimly lit museums—but the plot remains the same. And by 1:30 PM, I'm left with two familiar endings: either hoping he texts or dreading the text I need to send. The real kicker is that he always feels the opposite. When I like them, they don’t like me. When they like me, I don’t want them. (It’s funny. Right? Go ahead, laugh.)

My friends often find themselves in similar situations, where they consistently choose the wrong guy and let down the “nice” ones. Have my qualms infiltrated them? Or are we all doomed to fall for the men infected with New York’s dating scene plague? (Men hopping from woman to woman, infecting them with their bite of false promises and forehead kisses). 

I can’t answer for others, but I can for myself. Why do I spend the same repeated 18-hour window with Mr. False Promises as Mr. Good Morning? I’ve been enamored by many Mr. False Promises and bothered by multiple Mr. Good Mornings. But where these two types seem totally different, deep down, I know it’s always a one-time occurrence.  

My 18-hour first dates feel like reliving the first 20 minutes of a rom-com repeatedly, with a new cast every rewind. My anxious mind finds comfort in rewatching the same show over and over again (seriously, when I tell you I rewatch season two of Fleabag once a week, I’m not kidding). (Also, hey me again, I know you do the same, so watch the judgmental eyes). Imagine you apply that same familiarity and comfort to a first date. We match, text, giggle, kiss, say goodbye, and then never have to see each other again.  

I’m a hopeless romantic who wants to feel swept off her feet in Maria Hernandez Park by a tattooed 28-year-old filmmaker time and time again. Sue me! But at the same time, I’m not ready (yet) to fall in love again. The 18-hour first date is reliving the best part of letting go with someone repeatedly, with no worries about what they might actually think of you. For a person who fears allowing herself to love and open herself to others, this version of Groundhog’s Day is at the top of my Letterboxd. 

When you can relive the on-screen-like romance without worrying about the sequel, the matching, and the late-night texts for a week feels like a drug, and I’m a repeat offender. Side effects include crushing on Mr. False Promises when he ghosts and avoiding Mr. Good Morning when he asks when you’re free again. But what you can always prevent is developing real feelings.  

I do want to be in love, but I’m still learning how to be open to love. This leads me to be the villain on occasion. (I could’ve figured this out on 18 different one-night stands, but I digress). But the main character eventually gets their arc, right? Give me time.

<3 SBM