“There wasn’t a right time, Lily.”
“I’d love to hear your idea of when the right time would be,” she says. “Now me, I’d wait until after we have sex and use it as an escape hatch. But that’s not your style, Miles. You’re more the wait until the last moment, have it fuck up all your hard work type of guy.” She laughs at this observation, and so do I—because it’s true. “Remember when you had two homecoming dates?”
“Most bittersweet night of my life,” I reply.
Junior year Homecoming will go down as the moment I knew Lily and I would always operate on different planes. My date, Ashley, wasn’t my girlfriend but it was trending in that direction, and I was hoping that Homecoming would seal the deal. Only problem was that my Mother couldn’t stand Ashley, feeling that she wasn’t worthy of being on our fireplace mantel, where she kept all of our pictures. So, Lily set me up with one of her friends to be the “photo date.” I ended up spending, what should’ve been, one of the greatest nights of my life running back and forth between dates—like something you’d see in a sitcom, with my sister and her friends providing the studio audience laughs. Lily watched from the sidelines, finding amusement in my inability to find a middle ground. Ashley eventually got hip to the game, cursed me out, and never talked to me again. I tried years later to befriend her on Facebook, but she declined it and changed her security settings so I couldn’t resend it.
“It was like watching a cartoon, Miles,” she says. “But that’s who you are, the guy who wants to make everyone happy in the situations that require a winner and a loser.” She checks her watch, smirks, and continues. “But that’s a topic we don’t have time for. So, what happened on your date? Did you at least think about having sex with her?”
I’m not gonna act like I didn’t think about having sex with her, and I’d be lying if I said I would’ve turned it down. But there are too many moving parts in my life right now, and having sex on the first date would only add to my stress. I tell Lily every detail of the date, wanting to get a female perspective. She makes jokes at the beginning, but by the end of the story she’s stone-faced and peppering me with thoughtful questions, making a genuine attempt to help me. She stops me when I tell her about the moment by the water.
“Did you kiss her?”
“Um, no.” She gives me a look of amazement, and not the good kind. More of a “how-the-fuck-did-you-make-it-this-far-in-life” kind of amazement. “I didn’t think she wanted me to. She was just trying to demonstrate something.”
“Yeah, how she likes to be touched.”
It’s not surprising that a moment of physical touch is the one she chooses to focus on, in fact, I’d be shocked if she didn’t. “Look, I’ve been out of the game awhile. I apologize if I’m not an expert in romantic cues.”
“You play things too safe, always have.”
There’s a knock at the door and Lily perks up. “Were you expecting room service?” I ask.
“Something like that,” she says with an evil smile. “More like a … study date.” She answers the door, and I can hear her exchanging pleasantries with a female. She returns with a girl that looks familiar, but I can’t place her. Her hair is short, she’s wearing wire rimmed glasses with no lenses, and a full on denim ensemble. If you closed your eyes, she’d be the type of girl you’d see on a subway billboard promoting diversity. I glance at her backpack and would assume it’s a study date, but I know better. After a brief shut down—and by “brief,” I mean about thirty six hours—Club Lily has relocated and is back in business. “Justine, meet my brother Miles.” Lily is behind her, rubbing her hands while looking her up and down.
“Hi,” Justine says nervously.
I wanna tell Justine to run and to thank me later. That the subject of the tonight’s study session has been changed to anatomy, more specifically her own, and once it’s over—after reality sinks in and the hormones level out—she’ll be left alone to pick up the pieces of her psyche. But, all I can manage is a smile and a nod. Lily tells her where the room is and that she’ll be along shortly. Once Justine is out of sight, Lily moonwalks to the bar, “Been trying to link that shit for a month,” she says. “It’s going down tonight little brother.”
“Can we just finish our conversation?”
Lily nods, “Look, I’m not gonna lie to you, that universe thing sounds like a crock of shit.”
“All I’m looking for is honesty.”
“Alright. It sounds like she was trying to get fucked, but she didn’t want you to judge her, so she tried tricking you into making the first move.”
Wasn’t expecting that one. “Can you, for once, act like human connection is a real thing? Go ahead, give it a shot.”
“You’ve been out the dating game too long, Miles. Human connection is a ‘90s concept that’s only adhered to by Evangelicals and the Amish. Access is the name of the game, and right now she’s swiping right on some guy named Kyle, who has a little dick and a lifted truck. Now, he’s gonna come over and cash in on your ignorance. Congratulations, you’ve done your good deed for the day.”
I’m confused, wondering how many Kyles I know and what they drive. But I quickly give up. “Swiping right? What the hell are you talking about?”
She pulls out her phone and shows me an app called ‘Tinder,’ explaining how people are matched and swipe left or right depending on their attraction to the person. I can understand why Lily has it on her phone, the easy access with minimal interaction is too enticing to resist. We often laud technological advancements, but never acknowledge that everything evolves—this includes the dating world. No more buying drinks, having conversation, learning about each other as people, and building a connection. Just a cursory glance at cropped photos with more filters than a pack of Camels, and the decision to proceed is made with the swipe of a finger. “Ten times the ass, with ten percent of the work,” she adds. “It’s the world we always dreamed of.” I neglect to point out that was the dream of horny high school kids who should have matured enough to cultivate healthy relationships.
This is the world I’m entering—a decade behind everyone else—like I’ve been released from the penitentiary, trying to learn on the fly but feeling more helpless by the second. I should sell my possessions and live abroad on the fringes of society.
I don’t know why I thought Lily would be any different after all these years. Maybe I thought going off to college and living outside the bubble our parents kept us in would change her outlook on life. But Mom’s financing her education, so I’m starting to think she never left the bubble long enough to figure it out. Lily loves being the center of attention, and, when you combine that with her short attention span, it creates a toxic cloud that poisons those closest to her.
“So, you’ve had your date?”
“Yes.”
“And you wanna see her again?”
“Yup.”
“Then, what’s next?”
“I’m gonna text her and see if she wants to go out again,” I say, confident that I have the right answer.