3
By the time Nora shows up, we’ve already won three rounds of trivia and backed out of the fourth. Jonathan insisted on giving another team a chance at the free drink tickets, the prize for the winners of a round. Meg’s made great use of our collective earnings, and recently returned to the booth with another tequila shot. I’ve lost track of exactly how many she’s thrown back, but that’s okay. It’s good, actually. Meg spends so much time thinking about other people, it’s nice to see her let loose and enjoy herself, especially given her circumstances. That being said, if Teacher Phoebe were on the clock, she’d be reminding Meg to use her indoor voice right about now.
After taking a few shots in solidarity, Jonathan and Nora sip their beers while Alex nurses his signature cosmopolitan with a lime wedge. Jerry once confessed to me that it’s not technically a cosmo at all but actually Tito’s mixed with two packs of an off-brand cranberry Crystal Light. No one’s had the heart to tell Alex that his Carrie Bradshaw–inspired cocktail is a knockoff vodka cran at best, and a one-way ticket to prediabetes at worst. While everyone else works on their buzz, I trace little hearts into the condensation building up on the glass of my school night Diet Coke. I’ve learned the hard way that even the smallest of hangovers is lethal when you have no choice but to exist in a room full of four-year-olds all day.
My mind wanders to the letter in my dresser drawer while Nora fills the group in on her latest Hinge date, and I push the thought away before it gets the chance to ruin my night. Don’t think about the letter, I tell myself. Focus on Nora’s story.
I pivot my entire body toward her, hopeful that whatever she’s about to say is juicy enough to hold my attention. Knowing Nora, I’d say the odds are
in my favor.
“He wasn’t as cute in person.” She pauses for a second to apply a thick layer of shimmery gloss to her full lips. “And he had a boring personality to match. We ended up staring at each other in silence until I had no choice but to whip out Meg’s ‘questions to ask on a date’ note.”
Meg claps. “Told you that would come in handy!”
“So I sat there conducting a formal interview until the check came, which we split.” Nora spits out the last word like she just tasted something bitter.
Gasps sound from around the table.
“Oh my god, that sounds terrible,” I say, hoping my face doesn’t betray the smidge of relief I’m feeling. I know I should find no pleasure in Nora’s misery, but I can’t help but be comforted by dating stories like this one. They make me feel like I’m not missing out on anything too great.
“It really was. And he’s terrible in bed.” Nora shudders.
Jonathan raises an eyebrow. “Oh?”
Nora closes her eyes and takes a deep breath. While she never shies away from sharing the details of her latest hookups, I get the sense that she’s completely exhausted by the dating scene. I want to reach across the table and shake her. Don’t you know that I would trade places with you in an instant?
“The sex itself wasn’t even the worst part!” she continues. “When I was trying to get him to leave, he got himself a glass of water, placed it on my nightstand on my side of the bed, and tucked himself under the covers.”
“Oh god,” Alex says.
“It gets worse,” Nora goes on. “Right before he turned off my lamp, he asked if I”—she pulls out air quotes for this—“ ‘would mind keeping an eye on his breathing throughout the night.’ ”
“For any particular reason, or…?” Alex asks.
“He has sleep apnea or whatever it’s called and has to sleep with one of those giant machines.”
Jonathan chimes in. “There’s no way this story doesn’t end with him realizing he has to go back home to sleep with his robot, right?”
“You’d think so, wouldn’t you?” Nora takes a big swig of her beer.
“Instead, he reached over, turned off the light, and asked me to wake him up if I noticed any ‘unusual breathing patterns or sounds.’ What am I, an EMT?”
She’s joking, but deep down, I know Nora’s disappointed by her recent string of unsuccessful dates. She’s remarkably sure of herself and fiercely independent, but at heart, she’s just a big softie who wants to find love as much as the rest of us.
Meg slams her empty shot glass down on the table.
“There’s no fucking way!” she exclaims, and every head in the bar turns toward the commotion in the center of the room. Meg raises her empty glass
to the onlookers.
I give Nora my honest thoughts.
“Doesn’t it feel kind of nice that a man would risk dying in his sleep to spend the night with you?” I would go through this experience ten times over if it meant I’d be having sex in my twenties, and I’d do it with a smile on my face. I’d even buy one of those breathing robots to keep in my room.
“No,” they all say in unison.
“That is actually the worst thing I’ve ever heard,” Jonathan says to Nora.
Everyone chuckles in solidarity, seeming to agree with his sentiment.
“I woke him up at five a.m. to tell him I was late for Pilates,” Nora says.
“Why didn’t you tell me you started doing Pilates!”
“Because I didn’t start doing Pilates, Meg.”
“At least it makes a funny story?” Alex shrugs.
“It happens to the best of us,” Nora says as she turns to Jonathan.
“Remember Angela from sophomore year?” she asks, and Jonathan groans in response.
“Was that the one you found hiding under your bed a week after you
ended things with her?” Alex asks.
“No, that was Jen.”
And so begins the roundtable of dating horror stories.
I have protocols in place for when these types of conversations arise, which, considering we’re all supposed to be in our Sex and the City era, is pretty often. Usually I navigate these situations by relocating to the Pac-Man
machine outside the men’s restroom. Sometimes Jonathan even brings loose cash for me just for this purpose.
But tonight is different. Tonight, I stay at the table. Tonight, I force myself to listen to everything I’m missing out on.
Alex recounts his recent hookup with the Postmates driver who delivered his chicken Caesar wrap.
Meg contemplates if she should accept her terrible boss’s offer to set her up on a blind date with his son.
Jonathan informs us that Raegan, an obsessive old flame whose number he ended up having to block, recently found his work email.
My mind starts to wander in the middle of Nora’s impassioned speech about her new idea for a dating app. Something about men needing a letter of recommendation from at least three women before being accepted.
“You okay, Pheebs?” Jonathan asks as Meg accepts a glass of red wine from Jerry.
I was thinking about the letter in my bedside drawer.
“Yes, sorry,” I tell him. “My mind’s a little all over the place.”
“What’s going on?” Alex asks, and the genuine concern in his eyes has me spilling my guts in an instant.
“I got a letter in the mail today,” I tell them with a sigh. “It was from myself; I wrote it when I was eighteen. For a school assignment.”
I cast my eyes down toward my lap, wishing my Rugrats tee had a hole I could pick at.
“How fun!” Meg exclaims, having lost her ability to read the room somewhere between the tequila and the wine.
Alex gives her leg a reassuring pat. “Well? What did it say?”
Through gritted teeth, I tell them. “ ‘Lose your virginity.’ Period. ‘That’s all I ask.’ Period.”
The table falls silent, and it’s the kind of silence that I’ve become all too familiar with over the years. The kind where no one knows what to say.
“Not the periods…” Jonathan tries to lighten the mood.
I put my head in my hands, and everything comes out muffled. “It’s like I knew back then that it was never going to happen. And I keep thinking about
telling eighteen-year-old Phoebe that she’s still a virgin at almost thirty. She would hate me. And I don’t blame her. I hate me, too.”
“Hey.” Jonathan pulls my arms away from my face. “She wouldn’t hate —”
“And Sandy wants me to focus on all the positives in my life and make a list of all my accomplishments, as if that would help.”
“I think that’s a great ide—” Nora starts.
“It’s an insult to the art of list making.”
“I think that when you finally relax about the whole virginity thing, that’s when it’s gonna happen,” Alex says.
Meg nods in agreement. “You know what they say…” She pauses to think. Right when I’m starting to think she doesn’t actually know what they say, she gets there. Kind of. “A watched pot never blows up.” Alex slides her wine away from her when she’s not looking.
“Meg is right,” Jonathan says. “You’re too focused on it. You have to take a step back and let it play out the way it’s supposed to.”
I let his words sink in.
“And what if it never plays out?” I ask. “I can’t take a step back and wait for something that might never happen. There must be something I can do.
Ideally within the next thirty days.”
Nora laughs to herself. “How to Lose Your Virginity in Thirty Days, starring Phoebe Berman,” she says. “Now, that’s a movie I’d pay good money to watch.”
I freeze, my eyes locked on Nora while the neurons in my brain start to fire at a rapid speed. “What did you just say?” I ask her.
Nora pales. “Too soon to joke? I’m sorry, Phoebe, I—”
I cut her off. “No, Nora, you’re a genius!”
I walk over to the other side of the table and kiss her on the mouth. My face-framing strands of hair get stuck in her lip gloss.
“I am?” she asks as I reach under the table to grab my bag. I dump the contents on the table, all the supplies I could possibly need spilling out in front of me. I reach for the unopened box of felt-tipped markers.
“Oh my god!” everyone cries in unison as I rip open the packaging.
“Phoebe, what’s happening?” Jonathan asks, but I’m too focused on the task in front of me to answer. I take a single piece of printer paper out of my accordion file organizer, and with a purple felt-tipped marker, I begin to write the title of the life-changing project I’ve been waiting for:
Phoebe’s Guide to Losing Her Virginity in Thirty Days
A Checklist
I hold up the paper, angling it the same way I would a children’s book during a read-aloud so everyone can see it.
“What is it that I always do when I need to get something done?” I ask them.
Meg claps her hands together. “Make a list!”
“Exactly,” I tell her, and I wish I had a gold star sticker to give her, but those are in my sticker bag. You should always bring the sticker bag, I chastise myself. “So why not make a list for the one thing I need to do more than anything else?”
“So just to be clear”—Jonathan clears his throat—“relaxing and letting things happen naturally is completely off the table?”
“Oh, Jonathan.” I look at him lovingly. “It was never on the table.”
“I guess this could actually work,” Alex says. “A list has never failed you before.”
I lift up the piece of paper, and it shakes along with my trembling hands.
“This will be a list of tasks,” I explain, the intricacies of the plan becoming increasingly clear to me as I go. “The more of these tasks I do, the higher the chances are of me having sex in the next thirty days. And I already have some ideas.”
I reach for a different colored marker to begin making the official list.
“There are a few things from my romance novels I can put on here. Like, Rear-end a guy and exchange information.”
I write that down in my neatest handwriting.
“Or maybe it can be something as simple as Compliment a stranger on
his outfit.”
I write that one down, too.
“I hate to say it, Pheebs, but you need to add Go on a dating app date,”
Nora says. “That’s really the only way any of us are getting laid these days.”
“Noted.” I write it down, grinning from ear to ear as the list begins to take shape. I also add Redownload Hinge near the top.
“Maybe now you’ll finally go out with Matthew!” Alex adds. My stomach does a little flip at the mention of his name. “You did technically match on Hinge. You can see him next week when you’re home in New York for the wedding. It works out perfectly.”
I shake my head. “That ship has sailed,” I tell Alex, knowing full well that I already messed up any shot I had with Matthew by bailing on that date last year. “We’re just friends.”
“Oh, please,” Alex scoffs. “If he was just your friend, you wouldn’t giggle at your phone like a teenager every time you get a text from him.”
“I don’t do that.”
“Yes, you do,” Jonathan adds matter-of-factly. I shoot him a look.
“Plus, he wouldn’t be texting you every day if he thought you were just friends,” Nora adds. “Guys don’t do that.”
“We mostly only send each other our Wordle scores,” I tell them, even though that isn’t really the truth. Our main priority is the New York Times crossword, followed by Word Hunt, followed by Words With Friends, and then Wordle. I’ve also fallen into the habit of sending him tons of Star Wars memes I don’t totally understand but know he’ll enjoy based on a detailed analysis of his Twitter likes.
He sends me stuff, too. In fact, he sent me the video of Bev, the giant Pacific octopus I spent the entire summer obsessing over thanks to her ability to solve a Rubik’s Cube in 5.24 seconds. I’ve never been able to solve one myself, something I’ve spent plenty of time lamenting to Matthew. Maybe we should pay her a visit, he had texted along with the video. I became fixated on it, because if an octopus could solve a Rubik’s Cube, maybe I could, too.
Maybe I could do a bunch of hard things if I set my mind to it. I was inspired.
And so earlier this summer, when Nora and Meg made a drunken decision to get tattoos, I went with them. Now, tucked away in the crook of my left arm, I have a tattoo of a tiny octopus holding an even tinier Rubik’s Cube. The whole thing is small enough to be mistaken for an oddly shaped birthmark but large enough to have made my mother stop talking to me for two weeks.
Matthew got a big kick out of it, though.
But that’s it. That’s the extent of our relationship.
Our friendship, I should say.
“If it makes you all happy, I can add Go on a date with Matthew to the list,” I concede. “But it would definitely be more of a friend date at this point.
There’s no way he’s still interested in me after all the time that’s passed.”
“Of course he’s still interested,” Nora says. “But you better act fast and snatch him up while he’s still on the market. And if you don’t go out with him, maybe I will. He’s hot.” She smiles. I don’t smile back.
“You can add some easy stuff to the list, too, as a warm-up,” Jonathan suggests. “Like Flirt with someone at work.” I nod as I write down his suggestion, already thinking of flirty things I can say to Teacher Rob, the only male teacher we have. At sixty years old, he may not be the most ideal target, but he’s all I’ve got.
We spend the next half hour brainstorming ideas. When we’re done, I add one final bullet point to the bottom of the list: Advertise myself on Craigslist.
“I’m not letting you do that one,” Jonathan says before I even finish writing.
“That’s the great thing about this list!” I feel myself coming alive the way I only do when I’m organizing. “I’m ordering it from easiest to hardest, and the last few tasks on the list are worst-case scenario. Ideally, I’ll only have to complete a few of the easier tasks toward the top of the list.”
I point to one of the easier tasks: Compliment a stranger on his outfit.
“For example, let’s say I tell the cute barista from Alfred that I like his shoes. This opens the floor for him to say, ‘Thanks, I like your Shania Twain T-shirt. Would you like to have sex sometime?’ We go on a date to that sushi spot Jonathan and I have been begging everyone to try. After dinner, he walks me back to my apartment, and he leans in to kiss me when we get to
my door. I panic, but it’s okay, because he finds it endearing. He says we don’t have to do anything physical until I’m ready. We spend every day together, and the more time I spend with him, the more comfortable I become expressing myself physically. Fast-forward thirty days and I’ve lost my virginity to the cute barista, and all I had to do was check off two tasks.” I draw two check marks in the air with my finger to signify the completion of Compliment a stranger on his outfit and Go on a date with one of the meet- cutes from above. “And no Craigslist ads were made in the process.”
“Right, but what happens if the cute guy in the coffee shop doesn’t proposition you for sex immediately upon meeting you?” Nora asks. “You have to promise us you won’t give up.”
“The beauty of the list is that if one thing doesn’t work out, there’s always another! Any of these tasks have the potential to get me to my goal.”
The more I explain the details of the list out loud, the more I want to kick myself for not having had this idea sooner. I should have known that the one thing capable of lighting this kind of fire under my ass would be a good old- fashioned, goal-oriented checklist.
“I really feel like it’s gonna happen for you,” Nora says earnestly before switching to her signature sarcasm. “Plus, you’ve literally been oozing sex appeal recently.” She smirks and gestures to my oversized Rugrats shirt, which she tried to encourage me not to buy.
“Haha,” I respond dryly. Nora’s always going on about how I should be “showing off my assets” more, but that’s just Nora. I don’t take offense to anything she says. Even if it is directed toward my precious T-shirt collection.
I can hardly contain my excitement as I continue adding potential tasks to the list.
“It’s like a game of Candy Land! There are infinite routes to the end.”
A wave of calm washes over me as I admire the rows of evenly spaced bullet points, and everyone’s eyes move from left to right in synchrony as we read through the finished product.
Except for Meg’s. Her eyes move from right to left.
“I don’t like this one.” Jonathan points to one of the tasks in the middle of the list, one that I’d made sure to write down without anyone else’s input: Get drunk and make out with a stranger.
“You hate the way you feel after a drunk make-out,” he says, and the rest of the group nods in agreement. It’s true. I find it highly unromantic. But for the most part, the only way I’ve mustered up the courage to do anything physical with a guy is by getting drunk beforehand, and even then, I always seem to sober up before the situation goes too far.
“Well, hopefully it won’t come to that,” I tell them.
Alex reaches for my hand across the table. “I’m really proud of you, Phoebe.”
Meg, sucking on an ice cube from someone’s empty glass, agrees. “This is the most determined I’ve ever seen you.”
She reaches for the remainder of Alex’s cosmo and downs it in one sip.
Alex shoots the rest of us a silent, wide-eyed plea. Everyone pulls their drinks closer to their chests, away from Meg, except for Jonathan, who reaches out to grab my shoulders.
I can’t help but notice the way his thumb brushes lightly against the side of my neck. “Just promise us that you’ll still have time for us with all the sex
you’ll be having.”
“I will always have time for you guys.”
Of course I will.
Meg raises Jonathan’s beer. “To Phoebe getting railed.”
Everyone else follows suit. “To Phoebe getting railed!”
“To getting railed!” I echo.
Phoebe’s Guide to Losing Her Virginity in Thirty Days
A Checklist
Redownload Hinge Practice flirting with Teacher Rob Pet a dog with a cute owner and strike up a conversation
Compliment a stranger on his outfit Flirt with someone at Jamie’s wedding Find the cutest guy on the plane to help me with my luggage
Leave my number for a waiter
Get a random guy to buy me a drink
Get drunk and make out with a stranger Rear-end a guy and exchange information Go on a date with one of the meet-cutes from above
Go on a dating app date
Go on a date with Matthew Advertise myself on Craigslist
