Mastering the Art of When to Fuck

After four years of twirling my way through high-end bars, sipping martinis, and hanging off the arms of expensive men, I never would have imagined I’d end up back in my hometown.

It was the end of May, exactly two weeks since Boston and I had said our goodbyes. Since then, I’d signed up at a local gym, visited all three of my old high school friends, and rotated between sitting on the couches of any willing family member who’d have me. I was bored. I’d known this day would come eventually, but I hadn’t expected it to be so soon.

That boredom brought me out on a Wednesday night to what was my town’s version of a high-end bar. There I was, perched on the hard leather seat of a swivel stool. I was at the bar alone—something I hated to do—but I took a sip from my Cosmo and let the burn from the vodka chase away the nerves.

The bar wasn’t particularly busy. A few singles were scattered along the counter, maybe also testing their luck on the dating scene. I glanced to my left. There sat a man. Plain. The kind of face you’d expect to see peering over a cubicle. His hair was combed into a deep side part, the salt-and-pepper strands plastered in thin lines across his head. I wrinkled my nose and turned. 

To my right a fellow twenty-something was nursing a half-finished Cosmo. I nodded appreciatively. At least the girl had good taste. She sipped it absently while scrolling through her phone, her nails clicking lightly against the screen.

I sighed. I’d given up on the idea of finding a romantic prospect tonight, but maybe I could at least make a new friend. I opened my mouth to say something when she suddenly looked up, waved, nearly knocking over her Cosmo in the process, and called out, “Over here!”

A girl walked over, slightly disheveled, and immediately erupted into conversation. She wrestled her bag off her shoulder, draping it over the back of the barstool before dropping into the seat with the kind of casual ease that only comes with years of familiarity. I smiled. It reminded me of my college roommate—how we used to get shit-faced and then shit-talk too.

I took another sip of my martini and leaned in.

“Okay, so… remember that guy I told you about? From Hinge? The one with the cat that goes to RIT?”

“Yes! This is the one you’ve been out with a few times, right?” replied the Cosmo girl.

“Yeah, like… it’s been seven, maybe eight dates. And listen, it’s going great. Like, he picked this artsy little wine bar—super cozy, dim lighting, jazz playing in the background. I was like, ‘Okayyy, he really put effort in.’ And I actually do like him.”

“I’m sensing a but here,” the Cosmo girl interrupted.

“Well, we haven’t done anything yet.”

“What do you mean? You guys have kissed, at least. Right?”

The friend let out an exasperated sigh.

“Well, yes, but that’s it. It wasn’t even a particularly sexy kiss. No tongue. It’s all very PG. Like, I feel like he likes me, and we have so much fun, but he hasn’t made a move.”

Seven, maybe eight dates sounded like a long time to me, but really, what did I know? I shifted a little further to my right.

“Maybe he’s taking it slow,” the Cosmo girl suggested, pausing thoughtfully. Then she added, “You know what? Yeah, I think it’s even better that you didn’t rush it. That way, you really get to know him. Maybe this means he’s wanting something more serious. Have you asked any of your guy friends?”

The friend chuckled. “Makayla, what guy friends?” she asked.

So that was the Cosmo girl’s name.

“Point taken,” Makayla responded.

“Why don’t we ask the bartender?” Makayla added.

“Ugh, no. That’s so embarrassing.”

“Who cares? He probably won’t even remember us by tomorrow.” Then Makayla’s hand shot up in the air, and she fervently waved the bartender over.

The bartender sauntered by and asked, “Another round ladies?”

With a wicked glint, Makayla replied, “No, but we could use some advice,” and launched into the story again.

The bartender rocked back on his heels, uttering a single word: “Wow.” Dragging his hand over his beard, he paused, then answered.

“Yeah, I think it’s weird. Any girl I’m interested in, I’m not waiting eight dates to take her clothes off. I don’t know. Maybe he has a micro-penis, or maybe he just isn’t that into you. I definitely wouldn’t wait around to find out.”

I let out a snort. As riveting as the topics of micropenises and jazz dates were, the conversation left me pensive. The snippet of this girl’s life that I heard—or rather, eavesdropped on—for the last 30 minutes poked at something I hadn’t considered: How soon was too soon?

That age-old question gnawed at me for a few days, so I hit the field to gather research. I started with my college best friend. She laughed when I asked her, twirling the straw in her iced latte like the answer was obvious.

“Too soon for what?” she asked, arching an eyebrow.

I explained, “How soon is too soon to fuck?”

Her smile softened into something more reflective.

“Ugh, honestly? There’s no such thing as ‘too soon,’ because it’s always ‘too soon’ if it doesn’t work out. I think if a guy is gonna be shit, he’ll be shit whether you sleep with him on day one or in three months. If it feels right and you want to have sex, have sex then.”

She took another draw from her latte and leaned back in her chair with a self-satisfied smirk. I laughed and thought, Well, that’s the end of that.

I called my cousin and scheduled our routine Taco Tuesday happy hour. Pen in hand and guac-filled chip in the other, I posed my question. She tilted her head thoughtfully, a faint smile tugging at the corner of her mouth.

“You know,” she began, “I’ve had relationships that started every way you can imagine. Slept with someone on the first date, and we ended up together for two years. Waited for months before getting serious, and it still didn’t work out. And, of course, I’ve had the flip side of both—where things fizzled out no matter how we started. I’m not sure if I really know the answer to this or if there even is one.”

I asked my aunt. A woman not marred by Hinge, social media and the awful dating dynamics of a twenty-something. She didn’t hesitate.

“Wait. Take your time,” she said firmly.

“People can seem great at first, but you don’t really know who someone is until you’ve spent enough time with them. And I mean real time, not just dates and texts. It’s easy for anyone to be on their best behavior in the beginning.”

I mulled over the conversations but felt no closer to finding my answer. Did waiting longer or fucking sooner have any real implications for how a relationship would turn out? Did waiting make it more likely for someone to take you seriously, or could you wait too long and miss your window—like micro-penis man from the bar? Did any of it matter in the grand scheme of things?

A year later, I still revisit this question from time to time, and I’m still no clearer on the answer. Since then, I’ve moved to New York City and have been navigating the dating scene of the concrete jungle. A dating scene no less complex than quantum mechanics or the ethics of artificial intelligence. A dating scene that’s infinite fun with endless opportunities, but one that could absolutely chew you up and spit you out.

I think about the first man I dated here. Our first date went so well that I found myself across from him at 4 AM, slurping Bolognese and cheersing cabs. He came home with me that night, but I held back out of fear of being labeled easy. I slept with him on the second date, though, and to my surprise, he didn’t scream “whore” and drop me like a sack of potatoes.

We continued to see each other for months, and that relationship blossomed into something really special. We fucked, we fought, but most of all we had fun. Admittedly, it soured after some time, but looking back, I don’t think it would have mattered if I’d slept with him on the first, second, or tenth date. We had a connection, and both dove headfirst into exploring it.

The second man I dated I’d known for months. We went on many dates, and I never really felt sure about him, but I gave it a shot. We slept together once, then twice, and then never again. I had taken my time, gotten to know him, fucked him, and realized we didn’t fit. Sometimes you don’t know until you try, and in this case, knowing him longer didn’t make it any more likely that we’d work.

So, what’s my consensus? How soon is too soon? I don’t think there’s a one-size-fits-all answer. I think you’ll know what’s right for the right person. I also think it’s okay to get the timing “wrong.” People are complex, and so are relationships. The expectation that the rightness of sex and the predictability of relationships can be confined to the limitations of time is a one-way track to disappointment.

I don’t know when the “right” time is, and I think there’s a beauty in that unpredictability. To live on the precarious edge of taking that step and either barreling into something great or falling completely and catastrophically short. Personally, I think it’s worth the risk to test your luck. My advice: try sooner, fuck later, and see what works best for you.

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