Girl on Deck

Growing up is losing some illusions, in order to acquire others. — Virginia Woolf

No one ever imagines life at 23.

For one thing, it’s not a milestone age. It’s not 16, or 18, or 30. It just sits there, between 21 and 25, being depressed that Hallmark purposely neglected to manufacture a Happy 23rd Birthday! card. There’s a reason for that. They’d all look like this:

"Here’s to 23: you’re broke, living in your childhood bedroom and seriously wondering if being a prostitute would be that bad."

Congrats on not overdrawing this month!

Our deepest condolences on having no idea what to do with your life.

I would buy any of those cards. For myself.

Here’s what no one tells you about being 23:

College is over, and college was that thing you looked forward to your entire life. I mean, seriously – when was the last time a miserable 16 year old was told, Hey, don’t worry! You’ve got 23 coming up! Never, is when. College was the light at the end of the tunnel. Not 23. 

Then there’s that small, nagging detail called What now? When you’re 23, you’ve got two options: start working or go to grad school. If the concept of a career still terrifies you, I highly recommend grad school. It’s a great way to convince people you’re doing something productive when really, you’re just in a holding cell with other people who have no clue how to manage reality.

But worst of all – worse than anything – is that at 23, you have absolutely no idea who you are. One day you’ll look around and realize your entire life you’ve been on a train, and suddenly there’s no more track. So you either keep moving, hoping you’ll get your bearings at some point (but really just wishing someone would tell you where to go)...or you stop. Some people just stop. These people generally end up living in their parents’ basements, playing World of Warcraft and keeping Taco Bell in business.

In the interest of remaining above sea level, the smart ones attempt to carve out a new identity. That’s usually where the trouble starts. People who used to eat normally become probiotic, Paleo vegans. Guys who used to play sports get way too invested in fantasy leagues or Crossfit. The worst of them become runners. Have you ever thought about that? I swear, 97% of 10k participants must be in the twenties, because that’s all that’s on my Facebook and Instagram: the Turkey Trot and the Color Run and FitBit updates.

Honestly, I should’ve picked up running. Instead I picked the one diversion experts agree should never, under any circumstances, be considered a hobby: a boy.

PRE-SEASON: CHAPTER 1

I never make New Years resolutions, but every January I take stock of my life and make comparisons. That’s why, January 15, 2012, I took out my notebook—the one I was supposed to be using to take notes in class—and made a two-column list.

2011

Age: 22

Living situation: West Hollywood apartment, Los Angeles.

Roommate: Ellen (psycho who hoarded Girl Scout cookies and wouldn’t give me any; used a SodaStream on a regular basis. Clearly not to be trusted.)

School: Graduated from USC with an English degree—useful. Not.

Job: Nanny. Still a semi-acceptable profession for someone my age. 

Friends: Plentiful.

Alcohol intake: Russian czar-levels.

Boyfriend situation: None. Recently went on a date with someone who told me about their negative reaction to Prozac five minutes into our first drink.

Overall satisfaction with life: Cue the sirens. Things are dire.

2012

Age: 23. Have realized every birthday from now on will be more depressing than the last.

Living situation: Back in Boston with parents in childhood home; Spice Girls poster still on wall. Have barely any friends here.

Roommate: Two people in their 50’s; childhood cat now on brink of death.

School: Miraculously accepted to graduate creative writing program at top school in country – points! (So why do I want to throw myself out of a window every day?)

Job: None (grad school is a good excuse...should I go for a PhD next?)

Friends: Back hanging with grade school pals. Desperate.

Alcohol intake: Does vodka have vitamins? Is it possible to get all of one’s necessary nutrients from Red Bull?

Boyfriend situation: If stalking college crushes on Facebook counts, I have at least 12 boyfriends. 

Future plans: Going to the bathroom after this class.

Overall satisfaction with life: Satisfaction now equals three DVR-ed episodes of Real Housewives.

My life is a joke.

I put the notebook away because I was starting to get depressed. Plus, in two minutes class would be over and I had to get to Kyle’s. It was Friday and I had what I called a Connolly vacation weekend ahead of me. AKA, nonstop booze-and-boy fest. The only two things I looked forward to as of late.

Ugh. Even I was disgusted with myself.

Should I look into AA?

Could I write a book about AA? I imagined the title: Wasted White Girl: One Girl’s Downward Turn Into Vodka Red Bull Addiction. 

Could I become a millionaire off that book? Would they interview me on The View? Would this literally solve all my problems?

The sound of the clock broke my thoughts and I bolted from my seat.

I probably wasn’t an alcoholic. What a bummer. 

I’m looking forward to seeing what you guys come up with, Nancy called, but I was already halfway out the door.

Nancy, by the way, was my professor. My grad school professor.

Apparently in grad school it’s normal to call your teachers by their first name. I loathed the practice – it seemed like such a lame attempt at coolness. There seemed to be a direct correlation between Call me Jim! professors and impressive Dad Jean collections.

What I really hated though – what actually bothered me – was that it made me uncomfortable.

The first day of grad school, Call me Nancy had called us – the students – her colleagues. Panic rose in my chest the second she said this.

Shit, Nancy! I thought. You’re the teacher, I’m the student. We aren’t equals here, trust me. Seriously, are you high? Aren’t you supposed to teach me something? Don’t you know more than me?

And then, because I couldn’t suppress the thought:

You’re the adult. And I’m a kid!

That’s why I didn’t like calling professors Nancy and Jim.

Unfortunately, age wasn’t only one thing that separated me from everyone else in my program. Yet another glaring difference between me and everyone else – because that’s how I looked at this program, it was me versus them – was that I’d practically grown up on this campus, five blocks away from the classroom we sat in each day.

They were somewhere new and exciting. I was back to the stretch of sidewalk where I crashed my two-wheeler in 1993.

This city – and by extension, this school – represented a version of myself I never wanted to experience again.

Growing up in Boston, I was average looking. My hair was never straight enough, or blonde enough, or long enough. I had friends, but I didn’t play sports – pretty much the only way to be popular at my school – and spent most of my free time fantasizing about my grand arrival in New York, after I’d published my first bestseller at age 21. Naturally James Franco would get wind of this accomplishment and we would start dating immediately.

Contrast this with what my classmates were doing: busying themselves

planning Catholic retreats and figuring out whose house they’d get drunk at that weekend (Colin or Patrick’s?).

That’s how I ended up at USC, where my grand transformation took place. It was the furthest away, and the most opposite, of the world I’d grown up in I could think of. And once I’d left - once I’d gotten even three hours under my belt somewhere else - I vowed never to return to Boston.

Yet here I was – back here, enrolled at the school I swore to God I’d never attend.

But even that wasn’t the worst of it.

I could deal with Colin and Patick and Colleen and Mary. I could deal with the miserable winters and the fact that people here considered fringe something that goes on drapes, not on clothes.

No, it actually got worse; something I refused to admit to anyone (my parents, especially) and could barely admit to myself: how little I cared about school. How even though my parents were paying for me to be here, paying for me to delay real life...I just didn’t care.

It was astonishing to reflect on the person I had been in undergrad, back when I actually looked forward to school. Since starting grad school, I’d become the type of person I used to make fun of with the professors—the kind who constantly showed up late for class; the girl texting through discussions.

Everyone seemed dumb. I’d read everything they were teaching. I already knew how to write; no one here could possibly make me better than I already was.

Grad school felt like a waste of time, but the part that scared me the most was that it wasn’t like I had any sort of alternate plan. Grad school was the alternate plan. The original plan hadn’t exactly panned out, mainly because Looking for future NYT bestselling author was not a post I’d come across on Craigslist. 

Trust me. I’d looked. Multiple times.

My best years, I was starting to fear, might actually be behind me. 3.9 student, New Yorker intern, published writer...those things were in the past. Since leaving USC, I’d realized the truth: none of that stuff matters if you can’t make money. None of it.

So now I was 23 years old and washed up. No book deals on the horizon like I’d planned. No more LA, where I’d perfected the art of overachieving in every area. No more friends. They’d all stayed in California, or moved to New York, or were off finding themselves in some third world country. I hadn’t even suggested that plan, as I could predict my parents’ reaction:

We aren’t paying millions of dollars for you to ‘find yourself’ on vacation when we’re stuck here. Get real!

Then they told me if I was so passionate about India and helping people, I could go get takeout from Tandoor Charhouse for everyone and clean up the kitchen afterwards.

So that’s how I ended up in grad school. It was basically a yearlong stay-cation disguised as a productive activity. And I’d get a degree at the end of it. And it sounded impressive.

Basically, it checked all my necessary boxes. I signed up.

___

By the time I pulled my mom’s black Jeep into Kyle’s building’s garage it was starting to get dark out.

Thank God, I thought as I pulled towards the valet. Since the previous September, nighttime was the only time of day I looked forward to. I was like a bat. Or a vampire. A vampire who loved clubbing.

These were the kinds of thoughts that made me wonder where things had gone wrong. 

I should mention two things at this juncture: first, Kyle is a girl. The name works for her because she is stunningly beautiful and stunningly tiny. It’s a fact only gorgeous girls under 5’4 can get away with having a boy’s name. Since Kyle looks like Miranda Kerr and actually wears shirts from Baby Gap (as crop tops, but still) she’s the perfect boy name candidate.

On her, Kyle is ironic. On me, it would be tragic.

Second, in case the valet didn’t tip you off, Kyle’s parents are crazy-rich. East Coast rich. Kennedy rich. But what really kills me about the Connolly family is they play the part of rich people with such unbelievable attention to cliché. For example, not only do they go to events and serve on boards – they have a rich family’s freezer. It’s always full of things like duck profiteroles and stuffed mushroom caps. They stock appetizers for entertaining emergencies the way most people stock canned goods for natural disasters.

Kyle and I attended two years of school together: eighth grade and freshman year of high school. It would’ve been more, but for Rich People Only Reasons, Kyle was sent away sophomore year. This can be code for many things, but in Kyle’s case, it was code for caught blowing eight members of the lacrosse team blow jobs in the locker room.

At the same time.

Everyone was shocked when this happened, but I wasn’t. Kyle lived on the riskier end of the pre-teen spectrum. I mean, for God’s sake, she gave Patrick Mullen a hand job in the back of the coach bus on our eighth grade field trip to Plymouth Rock while I was up front taking a Which Olsen Twin? are you quiz in Seventeen.

But back to the blow job fiasco – after she was caught, she and the boys involved in the WASPiest crime known to humanity were expelled. That’s when things got really bad for Kyle. The boys terrorized her. They egged her house; they told everyone in our little private school bubble she’d slept with half the senior class; their little brothers made her sister’s life a living hell.

That’s the real reason Kyle went to boarding school in California – to escape. After that her family moved to the city, and no one heard from her until, well...now, I guess. We’d started talking again when I moved back from LA. In a twisted way only two white girls can, we reunited out of desperation for a post-college social life and a mutual desire to stay away from all our high school classmates.

This was back in September, and it had only taken one Connolly Vacation Weekend to figure out Kyle and I were the definition of a symbiotic relationship. Her parents loved me because I was a good influence friend – I’d graduated from a good school, I was getting my masters, I’d had several impressive-sounding internships and I hadn’t, to their knowledge, been involved in any sex crimes. I appeared to have my life together.

Ironically, I needed Kyle because my life felt anything but together – she was a fantastic distraction from the fact I had no idea what I was doing with myself. Contrary to parental belief, being in grad school doesn’t mean you have your life together. Sometimes it means you’re coasting on having done everything right in the past. 

All that being said, it really wasn’t surprising that I lived for these weekends at Kyle’s house. Her family owned a gigantic condo in Back Bay. It was situated right at the beginning of Newbury Street and overlooked the Boston Public Garden. The building had recently been restored to all its former art deco glory. Of course the Connolly’s had snapped up one of the units before construction was even complete.

By the way, how great is the term unit? When either of Kyle’s parents talked about it, it sounded like they were referring to a storage facility and not a sprawling 10-room apartment with half a million dollars worth of custom finishes and Viking appliances.

And that’s before they’d even hired the interior decorator.

And this apartment - trust me - had that interior decorator look. Everything was some shade of cream or taupe or gold. Interior decorators love that color combination. Actually, that’s how you know you’re in a house that was decorated all at once, and not piece by piece: even the soap dispenser in the guest bathroom coordinates with the fireplace poker.

Anyway, at this point I’d been to Kyle’s so many times that the doorman, Richard, didn’t even hesitate to ask where I was going when I walked into the gold and green marble lobby.

Kyle back? He asked as I walked in. We strolled together over to the elevator bank, where he pushed the up button. Kyle was the only friend I had who lived in a building where the doorman actually pushed the button for you. It always made me feel bad, like Richard was providing for 14 kids and I was the dumb brat he had to deal with to feed them.

Yup, I replied. She got back yesterday.

So I’ll see you guys around 5am, then? He replied. Then he winked, which was such a door man-y thing to do.

That sounds about right, I laughed. You know us too well! I called through the closing doors.

Upstairs, I walked into 14B without knocking. Knocking in this house was pointless. If Frank was home, he would be in the kitchen opening a bottle of wine or on the couch watching a football game. Kyle’s mom, Maggie, would be in her bedroom participating in some bizarre grooming ritual involving glycolic peels. Charlotte, Kyle’s little sister, was never home. She was always off at some concert, or hanging around with other misunderstood teenagers.

Kyle was just as predictable. She was always, without fail, in her room poking, prodding, or plucking at her already perfect body. It was better I just walk in unannounced and help myself to the ever-present assortment of gourmet snacks splayed out on the kitchen island. Seriously, everything in their kitchen seemed like it came from a gift basket. This family seemed to live on mini jars of grainy Dijon mustard and semi-stale pretzels. 

Kyle? I called as I walked in. I dumped my coat on the entryway bench and started towards her room.

I’m back here! She called. Sure enough, I found her in her adjoined bathroom. She was in her robe, all 5 feet 3 inches and 105 pounds of her, plucking eyebrow hairs I was pretty sure you’d need a microscope to actually see.

Hey, I said, dropping my bag on her bed. Since Kyle was still a senior at her school in Texas (she’d taken a personal year between high school and college) we didn’t get to see each other except on her breaks. This made our time together even better. There was something about our fun having a deadline that made it more exciting.

Nolan’s coming over in a bit, Kyle said, reaching for her hairbrush. I sat on her bed and watched as she commenced a routine rivaling Marcia Brady’s.

Oh, I said, trying to hide my irritation. Are we going out with him? I began pawing through Kyle’s clothes for anything I might like to wear more than what I’d brought. Shopping in her suitcase and closet was like an in-person excursion to the Nasty Gal warehouse. She owned things like $400 neon bandage skirts and $180 flowery crop tops.

Yeah, and my mom wanted to say hi to him first. He’s bringing two of his friends.

Oh, that’ll be fun, I replied, which was a complete lie. It wouldn’t be fun at all.

The truth was, I loathed Nolan – his brand of boy was one of the reasons I’d left the East Coast in the first place. At 16 he had a side part that should qualify for some sort of Brooks Brothers douche-in-training award, and he was the type who acted as if his dad being CFO of one of the biggest banks in the world was some sort of personal accomplishment. But none of this mattered, because Kyle had lost her virginity to him. I had to be nice. Plus, he was in love with her, and her parents were in love with him, but mainly because ending up with Nolan would mean Kyle would never have to work and could continue doing what she did best: being hot.

Yeah, Kyle said, crossing the room. "He’s so going to try and bone me. Ew."

I’m going to go shower in Charlotte’s room, I said, ignoring her comment. Duh, he was going to try and bone her. What guy wouldn’t try to bone her?

K, she said. Go see if my dad opened a bottle of wine. Let’s drink in the shower.

Okay, I replied, heading towards the kitchen. Sure enough, there was an open bottle. I poured two glasses of something I’m sure was too expensive to be in plastic into Solo cups and took a big gulp.

____

––––––––

Oh! Maggie called, clutching her manicured hand to her chest. "You girls look gorgeous."

That night it had taken us two hours and 39 minutes to get ready. A year ago, I could get ready in 40 minutes – maybe an hour if I were really being careful. But hanging out with Kyle made me realize I’d been living life in a fog of delusion that anyone could achieve hot girl perfection in such a short period of time. Clearly I’d been neglecting several crucial steps in the beautification process:

Sally Hanson Airbrush Legs: The concept was simple - make-up for your legs – but somehow I’d lived my entire life thinking a natural tan (summer only) and the periodic spray tan (special occasions) was enough to attract the opposite sex. Kyle taught me that, no, these things combined were nowhere near good enough. In order to achieve maximum hotness, I would henceforth be required to douse my legs in what was essentially orange spray paint. The results were amazing, so I didn’t argue. My white sheets however, had taken on a distinct, Halloween-themed hue. Small price to pay for legs that looked manufactured by Mattel.

False eyelashes: What once seemed a hassle now seemed a necessity ignored only by the ugly masses. My last trip to Boston Kyle and I made the pilgrimage to the Land of Beauty in Bulk (aka Chinatown) and purchased 60 sets of eyelashes each. $15 was nothing for the chance to enter a bar looking like a terrified deer.

Hair extensions: I had long hair, so what would I need extensions for? Well, I learned from observing Kyle, if long, thick hair is good, super long, super thick hair is better. Every night we dutifully clipped in our polyester extensions, then basked in the praise of people who didn’t realize our heads had become bigger fire hazards than a sparkler convention in a gas station parking lot.

Thanks, I said, smiling at Maggie. After weeks going make-up free and in questionably dirty yoga pants (grad school uniform...) I welcomed the acknowledgement. Kyle, however, ignored it.

Can I have some money, mom?

Yup, right on cue. Now either Maggie would give her what she wanted (a wad of cash) or they would commence a screaming routine right in front of me. Kyle would call Maggie a bitch, Maggie would call Kyle a brat, and no matter what was said, Kyle would end up with the money anyway. The best part of all of this was that during these fights, everyone seemed to forget I was even standing there. My role was to hang out inconspicuously next to the kitchen island, grazing from the expensive cheese plate. If anyone asked my opinion on anything, I’d give a non-committal shrug, agree with Maggie, then communicate to Kyle with my desperate, searing gaze, "No, you’re right!"

That night, however, Frank interjected with both a change of subject and $200 cash, which Kyle promptly stuffed into her Tory Burch clutch. I had to admit, it was an impressive tactic that seemed to diffuse everyone.

Is Nolan coming over? he asked.

Yeah, we’re going out with him and his friends tonight, Kyle replied.

Good, Frank said, uncorking another bottle of wine. As I’d long ago realized, it’s only considered alcoholism if you’re drinking off-brand whiskey from a brown paper bag. In families like this, it’s called entertaining, or, if no guests are over, food pairing.

Stay away from the athletes tonight, girls, Frank continued. I’m serious. They only want one thing.

"Jesus, Dad, Kyle replied, slamming down her plastic cup. Dark liquid sloshed over the edge and onto the marble countertop. Maybe if mom didn’t humiliate me every five minutes I wouldn’t have to stay away from them!"

He deserved that, Kyle! Maggie retorted. I took a sip of my wine.

Mr. Connolly, I interjected. Maybe if I changed the subject we could get the hell out of here faster. This wine is really good.

Kyle ignored my attempt at a peaceful resolution.

"Mom, you’re so fucking embarrassing! Don’t even make me bring up all the reasons that was psychotic again."

Here we go, I thought.

What Kyle was referring to, of course, was the now-infamous scene that played out a month prior at the Boston Bruins private Christmas party. As owner of the biggest restaurant group in Boston, Frank was on the permanent guest list for things like this. The Christmas party was the final straw in a series of events we now referred to as Malmo-gate, and it had all started the previous June at the Bruins Draft Picks and New Players Welcome Lunch.

Holy fuck, Kyle had said the day before the lunch, breathing heavily into the phone. Do you want to come to the Bruins draft party with me? My dad told me I could bring a friend.

Hell yes I wanted to go. I’d only gotten back to Boston from LA a week prior. My schedule consisted of Teen Mom reruns, followed by half-ass sit-ups on my living room floor.

So, yes, I wanted to go.

Kyle and I spent the follow morning primping (10am feels awfully early to apply fake eyelashes, but those are the HGR’s...hot girl rules) for what we were convinced was our shot as Bruins Girlfriend-dom. We’d be the only girls our age in attendance.

Does this dress look slutty enough? Kyle said, adjusting her boobs in her white bandage dress. 22 is a good age to wear skintight outfits in broad daylight. I can’t say I’d recommend the look to anyone with more than two years of legal drinking under their belt.

Definitely, I said with total confidence. It says, ‘I’m really classy, I could go to dinner with your parents,’ but it’s also really hot.

Good, that’s exactly what I’m going for, Kyle responded. Like, I want it to obvious that I’m from a really good family and but I also give head like a high-end hooker. Like, I’m not too uptight for that.

Exactly, I said. We stood in front of the bathroom mirror together, admiring our hotness. Well, I admired Kyle’s hotness, and marveled at my ability to turn myself into something resembling a Playmate.

Never in my life had I felt so fake...or so attractive.

___

Forty minutes later we found ourselves on the top floor of the Ritz Carlton, surrounded by Bruins executives, ex-Bruins, and current Bruins. And as we’d suspected, we were the only girls remotely close in age to any of the players.

All right, I said, my eyes darting around the room. Frank was in a corner, talking to Kent Wilkins, the team owner. Maggie was talking to Kent’s wife. If ever there were a need for a plan, this was it. We have to get a drink. We can’t just stand here.

Okay, Kyle said. We marched over to the bar.

Can we have two vodka sodas, please? I asked. So much for keeping it daytime casual.

A giant hand appeared on the cocktail napkin between us. We both turned to see its owner.

Henrik, he said, smiling between us. That’s all I got.

And that’s how Henrik Malmo, the Swedish wonder of the Boston Bruins, brought Kyle onto his roster. They had sex that night, after an evening spent drinking Grey Goose from the Bruins’ table at Royale.

Six months into this relationship and a week before the infamous Bruins Christmas party, Kyle and I were both getting concerned about one minor detail: Henrik had never actually taken her on date. Their time together was mostly spent between the hours of 2 and 10 am, when they would meet up at a bar, have a drink and promptly return to his place for a bone-a-thon.

He needs to take me on a real date, Kyle said, one particularly distressed Friday afternoon in November.

Okay, um, you need to lay down the law, I said. I’d had exactly one boyfriend in my life but had read enough relationship books to think I had any sort of clue what to do in this situation. Which, in retrospect, would’ve been nothing. Kyle was