The Time Cosmo’s Dating Diarist Went Sex-Toy Shopping on a First Date

·9 min read
Photo credit:  THE SCISSORHANDS - Hearst Owned
Photo credit: THE SCISSORHANDS - Hearst Owned

Catch up on the first three chapters here.

Saturday, 9 p.m.

Faithful readers may remember that I left off last time RSVP’ing to a “play party” hosted by Ethan, the gentleman from my threesome. But I now have a legitimate scheduling conflict. “There will be more parties, so I’ll hit you up again soon,” he says. Honestly...thank god. I need a few more months (and maybe a couple more threesomes) before I’m ready for a real New York sex party.

Meanwhile, it’s been two weeks since I last saw Steve and he left for off-the-grid Marine training camp, and I’m feeling extremely sexually frustrated. Or possibly just missing his company—it’s hard to tell. Either way, I’m ready to have myself a night. My friends and I are at our favorite neighborhood haunt, an Insta-worthy spot with a deeply classy clientele. The first time I was here, I asked the bartender for Fireball shots and he almost kicked me out on the spot. But now we’re buds and he gives me free espresso martinis.

Three guys come up and start talking to us. One, with soft green eyes and a gray V-neck, takes a liking to me. Or to my very see-through shirt that I accidentally paired with an orange mesh bra. His name is Matt, and after a couple of hours of tunnel-vision conversation, we’re shamelessly making out.

Sunday, 2 a.m.

Matt is now openly flirting with another girl at the bar. But nothing can bring me down tonight, so I’m just blissfully reenacting my Zumba class moves when a 6'4" guy with a single Elvis-like dangling hair curl approaches. “Hey! You’re gorgeous!” he says, grabbing my hand and turning my dance party of one into a joint venture. A man who can dance? My Achilles’ heel. He spins me, dips me, and kisses me. Damn, this newcomer has me All Shook Up (sorry, had to).

“What’s your name?” I ask as he pulls his head away from my lips just long enough for me to get a word in. “Matt.” “Wait, sorry, what?” “It’s Matt,” he repeats, loudly. I look over at Matt #1 and see he’s now fully entwined with the girl he was talking to. Guess we both moved on quickly.

Sunday, 11 a.m.

I wake up to two texts from two different numbers.

10:30 a.m.: “Hey. It’s Matt from last night. Any interest in having brunch with me?”

10:47 a.m.: “Hi Zara, this is Matt! It was great meeting you last night!! Would love to take you out. Are you free tonight?”

Photo credit: Hearst Owned
Photo credit: Hearst Owned

Well, shit. I only want to say yes to Matt #2, except I have no idea which number is his. But I have a case of the “fuck it, why nots,” so I decide to reply to both of them.

Sunday, 2 p.m.

Turns out, brunch is with Matt #1. In the daylight, I quickly confirm that whatever chemistry we had has fizzled into friendship. Which is honestly fine, maybe even great, because my superpower is converting failed dates into forever friends.“Hey, I need to pick up some things for my friend’s bachelorette,” I say. “Wanna join?” Matt #1 is game for turning our boozy brunch into a platonic sex-shop adventure. I pick up a dick-shaped water bottle to carry around while he suggests different toys, candy, and games.

Sunday, 7 p.m.

Dinner with Matt #2 is electric. I learn that by day, he’s a math nerd working an intense finance job. And by night, he’s going to raves and approaching life with an unbridled enthusiasm that reminds me of...myself? We can’t stop finding excuses to touch each other.

Somehow (lol), Ethan and the sex party invite come up. “Are you on Feeld?” Matt asks. “No...should I be?” I’m already balancing Hinge, Raya, Bumble, and The League. Do I really have bandwidth for another app? He shows me his profile and explains how it’s a pretty easy way to find threesomes, orgies, and parties. “I’m more than down to join you at future sexcapades,” he says. I don’t think a single other guy I’ve ever dated would’ve wanted to explore with me while partnered...or maybe they would have and I just never thought to ask?

Photo credit: Hearst Owned
Photo credit: Hearst Owned

“Want to get a drink at mine?” I offer Matt. He smiles and nods as he signs the check. Before my key is even through my door, he picks me up, wraps my legs around him, and starts kissing me while carrying me over to the couch. I straddle him, fully clothed. He reaches for the top button of my blouse, but I push his hand away. I want to tease him longer. I bite his lower lip and slowly start kissing his neck. I’m starting to run my hand over the bulge in his pants when he abruptly changes our position on the couch. “ I know this is going to sound crazy, but I need to tell you something.” Ah, okay. This can’t be good. Is he married? Does he have an STI? “I’m actually moving to Brazil...tomorrow.” I fall off his lap. Is he fucking serious?

Yes. Apparently, Matt is getting transferred to another division within his company. HOW DID THIS NOT COME UP AT ALL AT DINNER? Why did he even go out with me if he knows he’s literally about to expatriate from the United States within hours? “I don’t know,” he replies. “Something about your energy. You just seem like such an interesting person, and I had to get to know you better before I go.”

The worst part, I realize in a sudden emotional spiral, is that this has now happened twice in a row. I’ve connected deeply with two incredibly attractive, seemingly wonderful men who are leaving New York the next day. I mean, I know I put out into the universe that I wanted to commit to being single, to lean into a little loneliness and learn to find solace in solitude. But clearly, I’ve overcorrected. Here’s the truth: For the right partner, I would happily commit. I’m just now understanding that it’s not the commitment itself I’m scared of—it’s settling, of choosing someone who, like the doctor I broke up with a few months ago, is perfect on paper but with whom I know I’d be irrevocably unhappy in the longer term.

I’m in the middle of this existential crisis when I realize Matt is still on my couch. I need him to go home. He gingerly picks me up and jokes that he’s going to pack me in his suitcase. He kisses me one last time before leaving...for good. Did I google “flights to Brazil” immediately after his departure? Maybe, but then I remembered my hair does not thrive in humid climates and I get sun-induced rashes. I’m disappointed, but I remind myself that love, connection, and chemistry are abundant resources, at least in theory. I know someone else great will Matt-erialize soon (not sorry for this one).

Photo credit: Hearst Owned
Photo credit: Hearst Owned

The next weekend

I’m in Austin for my friend’s bachelorette party, and it’s a blast. We planned a scavenger hunt in our hotel, transforming each room into a destination that was special to the couple. Also, she loved the vibrator and toys, and everyone died when I told them I made a first date come with me to buy our goodies. I clearly put the “honor” in maid of honor.

Two weeks later, Thursday, 7 p.m.

I’m on a long-delayed first date with this guy Sean, a 29-year-old with sandy-blonde hair and blazing blue eyes. Ironically, he also works in finance, but his vibe could not be more different from Matt #2’s. Sean is more serious, more buttoned-up, but incredibly sweet. And he has the cutest laugh.

We were originally supposed to go out right after I ended things with the doctor, but I had to cancel to take care of my mom for an unexpected surgery (thankfully, she’s fine). At the time, Sean checked in every single day to make sure she was okay. (Bonus points for thoughtfulness.) When he recently slid back into my DMs to ask me on a date, I will admit my heart did an ever-so-slight baby backflip.

We have immediate, intense chemistry that is more than sexual. It’s intellectual. We sit at dinner for hours, geeking out over history, philosophy, the economy—arguably the most boring date subjects possible, but we’re cracking each other up. I just feel so at ease and giddy in his presence, and we seem to share a lot of the same core values. (Despite him leaning more politically conservative than I’d like, he did confirm he’s super pro gay marriage and a strong feminist, either of which would have been an immediate deal breaker for me if he felt differently.) Everything’s perfect until I excuse myself to go to the bathroom and proceed to rip my pants down the back while picking up an earring I dropped. Not a baby rip. A full Avril Lavigne emo-punk moment. It’s very noticeable, but Sean just laughs at my dramatic retelling of the tear. He offers me his sweater to wrap around my waist and walks me the 15 blocks home, leaving with a polite hug goodbye.

Friday, 3 p.m.

I honestly haven’t been able to stop thinking about the truly phenomenal first date with Sean. And evidently, it’s mutual. He’s already scheduled round two at an art museum for Sunday, and we’ve been texting flirty banter back and forth. Readers, I have a really good feeling about him. Could this possibly be the person I’m willing to actually try something more serious with?

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