“This is Lilly Pulitzer!” she said, waving her arm triumphantly over a hideous collection of dresses so garish and bright it was giving me a migraine. And even worse, everything was knee length. My style had devolved into two settings: emo and slutty. These contraptions were neither and I hated it.
I tugged a dress’s oppressively high collar. “I feel like it’s choking me!”
“It is.” Klo smirked. “It’s choking the hipster slut right out of you, Shallon.”
But I refused to spend three hundred dollars on something so stiff and unflattering, so I arrived at the Vineyard with a suitcase full of tatty boho dresses from three summers ago. They couldn’t be that out of style, right? Besides, Liv had never struck me as particularly Pulitzer-ian when we’d hung out before. So imagine my surprise when she picked me up from the island’s tiny airport in a pink polo and madras skirt. I, on the other hand, was wearing faux-leather leggings and a tank top with a skull on it. I looked like the town’s executioner.
I instantly regretted not getting the Lilly dress and realized that the last-minute trip I’d made to J. Crew wasn’t going to do much good. One pair of pink flip-flops wasn’t going to impress these people.
“Oh, don’t worry!” she said, reading my mind. “Our family really isn’t that preppy.”
I suspected that she was lying through her perfect teeth, but I gave her a grateful smile anyway. I heaved my suitcase into her trunk and noticed the license plate said CHPQDCK. Chappaquiddick. Not that preppy, eh? I was so screwed.
As we drove through the lush, verdant island, Liv tried again to downplay her family’s blue-bloodedness.
“Our house is seriously just a shack,” she explained. “Honestly, it’s nothing fancy; we’re going to just tear it down one day and totally start from scratch.”
“Shack” was not an accurate description of their beach house mansion. Perched on a cliff overlooking the quaint Edgartown harbor, their charming home was right out of a Nicholas Sparks novel. It was rustic and littered with sailing trophies, black and white photos of tight-lipped New Englanders, and nautical tchotchkes. It was like an architectural version of your favorite well-loved stuffed animal. I adored it.
Stairs led down from the main house to the boathouse and dock, where their two boats—a Parker and a Regulator, I learned—bobbed in the water.
“Dad and Tripp are out sailing, but hiiiiii!” Liv’s mother came skittering into the living room with tight, warm hugs for everyone. I adored her too. Lissie Potter reminded me of Kelly Ripa—small, blond, bubbly, and yet commanding respect and just a little fear. She was wearing an orange and white Lilly dress that I had definitely tried on and definitely definitely hated. It had made me look like a creamsicle on acid, but she looked marvelous. I could never imagine my mom in such a garment. Her favorite outfit was a silk romper from Bali that she paired with carved African bracelets and custom-made sandals from Capri.
Liv’s friends Kayla and Laura arrived a few hours later, and I immediately latched on to Laura because she was black and I assumed she would also feel out of place. Wrong again, Lester. Laura was the preppiest of us all, refusing to wear shorts more than three inches above the knee because they’re “terribly inappropriate.”
We spent the weekend lazing around at the Chappy Beach Club, a treasure trove of WASPy tittle-tattle, listening to Lissie point out who was sleeping with their babysitter and who was addicted to Xanax.
The other girls nodded vaguely, much more interested in soaking up sun than gossip, but I hung on every salacious word. If I was going to leave emo boys behind for good, I was going to need a preppy mentor, and Lissie was it. I begged her to teach me how to snag my very own trust-funder.
“I just don’t think I look like the kind of girls they usually date.”
Lissie waved off my worry with her bejeweled hand. “Honey, you’re on TV, remember? Celebrity goes with everything. You go, girl!”
Obviously, she was defining “celebrity” pretty loosely. At the time, I’d just finished filming the show, and no one had any reason to know/care who I was. But she was onto something. I should play to my strengths. I was never going to be the perfectly proper New England girl. Not without lots of Ativan, anyway. I was too bold, too brassy, too large of a presence. I decided to try to use this to my advantage.
Later that day was the annual Fourth of July flotilla—which I’d been mispronouncing as “flow-tee-ya” (thanks, Mexican food)—an event in which all the Vineyard’s young people sail out to Cape Poge and tie their boats together for a massive on-deck party. I put on a giant floppy hat and Prada sunglasses and practiced saying “No photos, please” in the mirror. With any luck, I could convince people that I was Lauren Conrad.
We motored up to the flotilla, already half-drunk on coconut water and rum, and one boy immediately caught my eye.
He was tall, broad shouldered, and pale with curly blond hair.
“He was a ginger,” Klo would later insist, shuddering with revulsion. But she’s a brunette and they’re too busy waxing their mustaches to understand the complex subtleties of blondness.
Whatever he was, I was intrigued. Oddly, it was his swimming trunks that caught my eye. They were neon green and looked a little like boxers—a far cry from the knee-length board shorts those California boys wore. With his nose stripe of zinc oxide and pink Wayfarer sunglasses, he looked like the jock from an eighties movie.
The shorts, Liv explained, were something called Vilebrequin, and the boy was someone called Wickham Brooks.
All my synapses fired at once. Wickham Brooks. I was sold on the name alone. Liv filled me in on his pedigree: grew up in Connecticut, went to some East Coast college where people wore blazers to the dining hall, worked as a hedge-funder in Manhattan. And he had two siblings, which meant that he was literally a Brooks brother.
I needed a closer look. I hopped gingerly across the boats to his vessel, where he was fist-pumping to “Danger Zone.”
Celebrity, celebrity, celebrity, I repeated to myself.
“Hey there,” I said demurely. “Do you have any ice? Our bottles of Cristal are getting hot.”
Wickham, still fist-pumping, got right up in my face. For a second, I thought he was going to kiss me.
“GONNA TAKE IT RIGHT INTO THE DANGER ZONE!” he belted at the top of his lungs, and head-banged away into a group of girls in Ralph Lauren one-pieces.
I sulked all the way back to our boat; was this guy seriously choosing a cluster of Merediths over me? I balled up my little fists like a villain in a Lifetime TV movie.
“You will be mine, Wickham!”
My second chance came a few hours later as we sailed back to Chappaquiddick and noticed two guys stranded in the middle of the ocean, floating on a small capsized sailboat. Everyone was too drunk to care and sailed on, until I realized one of the shipwrecked sailors was wearing neon green swim trunks.
“Tripp, turn the boat around,” I said. “My future husband is floating out to sea!”
Brilliant, I thought with a scheming smile. I’ll save his life and he’ll thank me by proposing.
“Oh my goodness, are you all right?!” I said dramatically as we motored up, fighting the urge to add Yes, it’s me, Shallon Lester, star of MTV’s hit Downtown Girls, to the rescue!
Clinging languidly to the boat’s broken sail, neither of them seemed too concerned about being stranded in the Atlantic; Wickham was sipping a Smirnoff Ice while his friend took a final swig of his Bud Light and tossed the empty into the waves.
“Do you guys have any more beer?” the friend asked.
“Oh yes,” I said. “All the beer you want … up here in the boat! The nice dry boat!”
I felt like the White Witch coaxing Edmund into her sleigh with Turkish delight. After a few minutes of cajoling, I finally convinced them to come aboard, where I attempted to make small talk with Wickham. Wasted and waterlogged, he wasn’t much of a conversationalist. But he was decidedly uninterested in me, which was all I neede
d to become totally obsessed with him.
“They’ll be out later tonight,” Liv said, trying to reassure me, as we dropped them off in Edgartown. “But uck, I don’t know why you like him; he was such a little shit when he was younger. I can’t imagine he’s changed.”
I thought about what my friend Ellen had pointed out one time: I don’t date people, I date types.
“You say ‘I want a preppy, I want an athlete,’ ” she explained. “But you never say ‘I want someone smart, I want someone funny.’ It’s like you’re shopping instead of dating—I’m running out for eggs, milk, a Rockefeller, and a pro lacrosse player.”
But my checklist methodology made dating easier, especially in New York. It helped you decide how to dress and where to go—Upper East Side for preps, SoHo for Eurotrash, East Village for unemployed musicians. Even back in high school I’d been a social chameleon, building sets with the theater dorks one day and sharing a limo to prom with Preppy Spice the next.
What else was I supposed to do? Judge someone based on their personality? Sweet cracker sandwich, I don’t have all day! Imagine the effort that goes into talking to every boy one meets without these categories as filters. The thought alone exhausted me. Besides, boys were always typecasting girls—blondes over brunettes (obviously), Jews over gentiles, tits over ass. If they could do it, why couldn’t I?
That night we ran into Wick at the Atlantic, a local bar stuffed to the gills with prepsters. He was clearly well on the road to black-outville, careening around the dance floor like a heat-seeking missile, before landing at Laura.
“You … you wanna make out?” he slurred.
“Uh, no,” she said, adjusting the pink ribbon in her hair.
Wick didn’t really take no for an answer. He grabbed Laura by the ears and made out with her face; I don’t know if you could really call it kissing, but it did involve lips, tongue, and spit.
She pushed him away and he toddled off as I burned with jealousy. But oh, my turn for some oral assault would come soon enough. After last call, everyone spilled out into the street and Wickham wandered up to us.
“I remember you,” I said coyly. “I fished you out of the ocean this afternoon.”
Before I knew it, his tongue was in my mouth and Liv was whipping out her camera to capture it. And then, just as quickly, he disengaged and was be-bopping down the street.
I wiped the slobber off my mouth and smiled, predatory schemes unfolding in my head. Oh yes, Wickham … you will be mine.
Phase the First being complete, once I got back to the city, I took the next logical step—stalk the bejesus out of him on Facebook. I refused to friend him right away, but he was dumb enough to leave numerous photo albums public, so my roommates and I spent that week doing research.
It became clear he wasn’t just a preppy, his blood was bluer than the man-made lakes of my Irvine youth. Every picture featured a sailboat, Nantucket Reds, guys who looked like Kennedys, or all of the above.
“Well, he’s no Lord Voldemort, that’s for sure,” Marcia said, clicking through his “Sailing to the Caymans” album.
“Meaning that he’s taller than five-foot-three and doesn’t look like a white version of Prince?” Pfeiffer quipped.
“I dunno,” Marcia said, squinting at a photo of Wickham and his dad in Antarctica next to their boat. “He’s just so … different from everyone you’ve dated.”
Exactly. Dating emo guys had yielded one disaster after the next, culminating with the Voldemort nuclear holocaust. I couldn’t go through that again, not ever. I needed a boy with no possible chance of getting to the real me, and Wickham was it. Wick seemed dull, immature, and two-dimensional—perfect for my fragile heart.
A few days later I put Phase the Second into action: I friended him on Fbook, adding a note: I know you … you Frenched my friend and me over the 4th in the Vineyard. Classy!
Within two hours, he’d accepted my friend request and sent me a message apologizing for the face rape. Before long, we were messaging back and forth every hour. By sunset, he had asked me out for drinks.
Phase the Second: complete. I tried my hardest to craft a modest, New England–appropriate outfit, I really did. But I just can’t resist dressing like a tart, so I turned up in a short skirt and heels.
I fully expected Wickham to be dreadful, but since I’d already named our future sons—Sebastian and Bridger—I downed a shot before leaving the house and hoped for the best. All I needed was a guy I could tolerate and parade around as my preppy trophy boyfriend. Nothing more, nothing less.
Really, I can’t tell you how disappointed I was to find Wick to be charming, smart, witty, and incredibly sexy. We talked for hours and kissed in the cab home; it took every ounce of my self-control not to drag him up to my bedroom, but I didn’t. The next morning, he texted me to say that he’d had a wonderful time and couldn’t wait to see me again, and before I knew it, we’d set up a dinner date for Friday night. Pfft, great. This was the last goddamn thing I needed—an actual, nerve-wracking, tummy-fluttering crush.
“Please, please don’t send him a creepy text like you always do,” Marcia begged. “He sounds rich and I feel like his apartment building has a pool and I’d really like that this summer.”
“Yeah, remember that time you texted that guy Steve ‘I can’t stop smelling my fingers’ after you ate barbecue at Brother Jimmy’s?” Pfeiffer hollered from the kitchen. “And then you were like, ‘Wahh, I don’t understand what happened?!’ ”
As my roommates howled with laughter, I decided against telling them that I’d already sent Wickham a creepy text. It just sort of … slipped out. During our date, he had told me all about his sailing adventure to Antarctica and we’d made a joke about polar bears and how he kind of looks like one. So naturally, thinking it’d be soooo cute, I had texted “Looking forward to dinner with a polar bear tomorrow night. I’ll bring some raw fish for you to catch in your big ol’ paws.”
Apparently he didn’t remember our bear talk one bit because he replied with “???” and I was sure I’d flushed my chances down the drain. I wrote back “Oh sorry, totally sent that to the wrong person! You’re next to my friend Wendy in my phone!”
As if that’s less creepy, Shallon. I suddenly dreaded our date. That idiotic text had drained me of any power or upper hand. He probably had the Ick so badly, and if he didn’t, I was sure he would once he got to know me. How could I relate to his world of polo ponies and country clubs when I’d only recently learned that Martha’s Vineyard wasn’t owned by Martha Stewart?
And then, just a few hours before our date, Jesus bestowed a miracle upon me: a sprained ankle.
I was kickboxing with my trainer, Reggie Chambers, when I rolled my ankle and had to get crutches. Even as I writhed in pain on the floor of the gym, I celebrated my stroke of luck. Injuries are a girl’s best friend when it comes to dating, and I hobbled home with a smile on my face; this orthopedic boot would put Wickham right where I wanted him.
I crutched into the restaurant like a wounded bird as Wickham leapt up in alarm.
“Shallon! What happened, are you okay?!” His face filled with chivalrous concern.
“Oh,” I said meekly, wobbling for effect, “I’m fine, don’t worry about me. How are you?”
He fussed over me the entire night, sitting on the same side of the booth and cracking my crab claws for me. The polar bear text debacle had been totally eclipsed by my fabulous new malady, but now a new problem was looming on the horizon: connection. True, real, person-to-person connection. Maybe my being physically vulnerable made him want to open up emotionally, but whatever the impetus, he and I talked for hours, about everything. Parents, dogs, work, guns, college, politics, oysters—everything.
That night when I got home I floated (as much as one can float on crutches) through the door, gushing details to Pfeiff and Marcia.
“I think I actually like him for him, not just the preppiness anymore.”
The girls looked worried.
I chewed my lip and tried not to think about it. Wick and I were bonding, and no amount of monogramming or madras was going to come between us. And for the next several weeks, nothing did. He was sleeping over most nights, and we were getting along so famously that I even took him to an MTV party.
And then … things started to fall apart. Admittedly, we were running out of things to talk about. The pauses during dinner got longer; the texts got shorter. The last night we hung out, we ordered in and watched 300, his favorite movie (FYI, any man worth dating will love 300; it means he loves his country, appreciates a strong woman, and has good abs).
The last thing I ever said to Wick—in person, anyway—was a line from the movie as he was leaving my apartment: “Come back with your shield, or on it.”
He laughed his deep, throaty, preppy guffaw and trotted down the stairs and out of my life. Sure, I knew we both had a busy few weeks ahead of us—I was moving and he was having minor surgery on his shoulder—but we’d make time; he could dope himself up on Vicodin and lay around while I unpacked boxes.
Or, he could turn into a giant baby and crab and whine incessantly until I flipped out on him.
Wick made his surgery sound like he was having adamantium grafted onto his skeleton, but I don’t really have a whole lot of sympathy for men who can’t withstand pain. What would King Leonidas say?
But still, I’m surprisingly maternal when it comes to the boys I date. I can’t help it; I’m a southern belle at heart. I enjoy having a boyfriend because I like taking care of someone, but I think this works against me; boys don’t expect me to be so sweet and often mistake it for obsessive love, especially New York guys. So I’ve conditioned myself to stay a bitch for as long as possible. But with Wickham, I thought we were past those kinds of games.
I offered several mellow, recuperation-friendly date ideas. He rejected each one, somehow getting grouchier with each response.
Exes and Ohs Page 11
