Phoebe Berman's Gonna Lose It(12)
“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