Cosmo’s Dating Diarist Might Be Ready to Commit…Unless a Butt Plug Ruins Everything, That Is
Catch up on the first four chapters here.
Sunday, 3 P.M.
Still riding a high from our fun, easy dinner date, I meet Sean (my 29-year-old blonde finance guy) again at the museum he’s suggested. I pack nips of Fireball in my bag. “You’re entertaining, I’ll give you that,” he laughs, as we clink our minibar-size bottles.
Ninety percent of the art here looks like it came out of a fourth grade class. I propose a game: Pick the most atrocious piece, and the other person has to make up its origin story. Sean has fully committed to the bit. He also keeps brushing his arm against mine.
We leave and head to dinner nearby and are deeply engrossed in each other when someone stops at our table. “Zara?” Oh my god. It’s Fulvio, the Italian man with whom my friend and I bungled a threesome years ago—in a literal Roman palace, no less. He kisses me on both cheeks and introduces himself to Sean as an old friend of mine.
It turns out Fulvio is stateside getting an MBA at Sean’s alma mater. Small fucking world. We chat for a bit before Fulvio joins his date by the bar. I’m itching, and I mean ITCHING, to tell Sean the full story. But I get the sense he may run more sexually conservative than I do, and I’m not sure how he would react. I bookmark this potential incompatibility...but it’s also possible I’ve read him wrong.
Sunday, 9 P.M.
We’ve now been at dinner for more than three hours. Sean is surprisingly vulnerable while telling me about his life, and he gives my own musings his full attention. I’m impressed by the self-awareness and thoughtfulness with which he speaks about his feelings. But...why hasn’t he kissed me? I feel like Sebastian in The Little Mermaid trying to orchestrate Prince Eric’s lip-lock with Ariel. Sha-la-la-la-la-la kiss me, Sean. He finally gently caresses my neck and pulls me toward his lips. I feel a small shiver through my body. Sean just woke up the dormant butterflies in my belly that haven’t been activated in a very long time.
I’ve become so conditioned to the mindset of being single, I forgot how scary it is to start really liking some-one—that weightless feeling as you fall into the abyss, knowing they could crush your heart at any moment. As we walk out, Sean intertwines his hand with mine. Ugh, I love a good kindergarten handhold. Guys, I’m a goner.
Thursday, 8 P.M.
After lots of flirty text banter between work chaos, I’m on Sean’s couch for a movie night. I’m trying to take things slowly on a physical level, both because I can tell it’s his vibe and because sometimes the longer the anticipation, the better the sex. Still, I’ve got brand-new Agent Provocateur peeking out of my blouse....Never mind. I fully fall asleep mid-movie. Definitely snoring, possibly drooling.
You know, it’s so easy to fall for someone amid a whirlwind of well-planned dates. (I mean, that’s literally the premise of The Bachelor.) And while I wouldn’t say no to a helicopter and hot tub moment with Sean, it’s actually this type of “comfort test” that matters most to me—the fact that I feel completely at ease just hanging out. I save my lingerie demo, thank him for the great night, and take the subway back to mine.
Sunday, 6 P.M.
We are finally engaging in an out-of-control make-out. Unfortunately, we’re also in public and in front of children. “Less kissing, more skating,” the roller-rink attendant yells. I suggested this activity for our fourth date, my lack of physical coordination be damned. But I keep strategically pushing him against the railing so I can catch my breath—and steal his with well-timed kisses.
So far, we’ve kept it to a firm first base. Not even a boob graze. And I’m not gonna lie—now I’m kind of stressed about having sex with him. First of all, what if it’s disappointing?Second of all, Sean has mentioned that he views sex as a monogamous, exclusive commitment, which means when we have sex, it’ll be like pulling the relationship version of an Advance to Go Monopoly card. I haven’t dated anyone else since meeting him anyway, but if things go well, that first sex with Sean could be my last new sex for who knows how long? Which also means no sex party with Heather and Ethan and no more exploration. But as he confidently skates backward and pulls me through the crowd, I think I might be ready to take that step with him.
“Can’t wait to see you again,” he texts me immediately after we say our goodbyes. Okay, fuck it. I’m all in. I’m ready to give my heart and body to Sean. Mark your calendars, team. Our next date is our sex date.
Four Weeks Later
So. I have not seen Sean. At first, we were both just incompatibly out of town, but now he’s breadcrumb-ing me: responding just enough to stay connected but being extremely noncommittal about concrete plans.
It hurts. I deserve better than being slow-faded into oblivion, because I am a person and any person deserves better but also because he and I seemed to have established a foundation of mutual respect, which makes this behavior feel even more insulting.
And after one final “Let’s do next weekend” from him evolved into “Sorry, I’m actually busy with friends,” I throwout a Hail Mary, hoping to inspire an honest conversation. “Cards on the table,” I text. “You’re the first person I’ve liked in a long time. I had hoped to get together again but sounds like it might be too difficult to coordinate.” He takes the bait: “To be honest....” We agree to meet in person.
Tuesday, 7 P.M.
Last month, Sean’s sister uncovered a very funny video I posted online where I tell a story that mentions a butt plug. Not me using a butt plug, but the concept is referenced nevertheless
(Also, my friends would like me to point out that this is not even my funniest butt plug story, but that’s a tale for another time.) Turns out, Sean’s family is very conservative, and I guess the firm he works at is notoriously scandal-averse. He says he hasn’t been avoiding me out of lack of interest or attraction. He’s been calculating the potential discounted cashflow from the potential impact of our relationship on his career and family. And as someone who’s comfortable joking about sex (like, you know, in this very column), it’s clear to me that on the balance sheet of his life, I’ve moved from a safe asset to a high-risk liability.
“Zara, this is really hard. I like you so much,” he says. He runs through his favorite qualities about me in a way that shows just how deeply he “sees” me. I’m watching him struggle with the reality of losing me. And I’m getting the sense that if I backtrack on the video, he might marry me on the spot. Or throw me on his bed and rip off my clothes. But instead, I say this: “I stand by the video. It’s hilarious. I am who I am. And I want a partner to celebrate my humor, not censor it.”
No matter how much I like him, I can’t be with someone who would ever feel ashamed of me. This closure is a double-edged sword—a mix of devastation and acceptance. Knowing with absolute certainty that you and a potential partner have irreconcilable differences is a gift, in a way. But it shouldn’t have taken a month of being brutally breadcrumbed to get here. “You’re amazing. This sucks,” he says, as he gives me a final, prolonged hug. I take a deep breath and exit his monochromatic man cave for good.
The Following Thursday
Tonight, I have a date with Johannes, a 42-year-old start-up exec who works inhospitality and definitely uses pictures from 10 years ago on his profile. He’s great though: funny, relaxed, radiating hot-dad energy. “I hope this isn’t creepy,” Johannes starts, “but I found a video you made, and I thought it was so funny that I sent it to my cofounder and all my friends.” And there it is. The sign of the century. (Yes, this is the same video that spooked Sean. No, I’m truly not making this up.)
Our chemistry may be too weak to form a strong foundation, but this date was worth it for reaffirmation alone. Deep down, I know that for the right person, I’ll never be too much.
One Week Later
“Are you still bringing your plus-one?” Shit. I forgot I was going to invite Sean to my friend’s wedding. “No worries!” The bride graciously offers to rearrange the seating chart. “I’ll move you next to the best man! He’s single. You’ll love him.” Well, well, well….
*For any new readers (hi and welcome), “Zara Field” isn’t really her name. All other names have been changed too.
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