When You Least Expect It Prologue I “Uggghhh” Weddings
When you live in New York City, it’s almost expected that people will see you at your very, very worst, very, very often. It’s built into the price you pay to live here, because you will at some point fall into the trap of believing that every block, every subway car, every splinter-ridden park bench is your own personal territory for having a full-blown mental breakdown.

I pinky-promise you that eventually you’ll stop thinking twice about walking down Third Avenue in the morning to buy a large cup of coffee, with your hair in a spider web of tangles and your bra everywhere but where it should be—which is on you. And you’ll stop noticing that everyone is staring at you as you publicly break up with the person who has had an iron grip on your heart. After all, if there isn’t a crowd of at least five total strangers watching, can you say it even really happened?

The comforting thing is that even when you’re at your worst, there’s always someone else one-upping you one block over. That’s why you don’t need to bat an eye when tourists turn their chunky DSLRs away from the Empire State Building and zoom in on your face, mid-ugly-cry.

I, however, am the kind of person who tries to keep my humiliations private. Like the time I had to be rescued from the bottom of my own closet.

“Hello?” I whispered in a delicate panic to the kind soul at the other end of the line at 9:00 p.m. on a Sunday. I had been organizing my long-neglected closet, only to be rewarded with every shelf collapsing on top of me, along with an avalanche of forgotten clothes that should’ve been donated to Goodwill years ago. The only parts of my body that hadn’t been temporarily paralyzed were my face and a single outstretched arm that had managed to reach my phone. I had dialed the only person I knew would pick up at that hour: my building’s on-call maintenance man.

“What’s the problem?” he asked, pushing a giant rock of phlegm up and down the bumpy lining of his esophagus.

“It’s an emergency,” I said, attempting to wiggle my toes beneath a pile of platform shoes that my friends and I had worn when we dressed up as the Spice Girls for Halloween. “My shelves collapsed, and now I’m trapped at the bottom of my closet.”

“Can’t you call someone else?” he asked, annoyed, clearly regretting giving me his personal cell phone number when I moved in.

“Well, I don’t have a—”

“A what? A boyfriend? A best friend? The ability to dial 911?”

I took a deep breath and imagined what would happen if I called 911 and they transferred me to the NYPD’s Seventeenth Precinct at 9:00 p.m. on a Sunday. I imagined what it would feel like to utter the words, “Help me! I’m trapped in my own mess of polyester and sequins,” to the city’s’ finest; how I’d have to beg and plead for them to stop handcuffing the guy trying to break into a non-twenty-four-hour CVS, or quit patrolling Fifth Avenue to come to the twenty-sixth floor of my apartment in Murray Hill just to rescue me from a pile of T-shirts I had bought seven years ago.

“Please don’t make me do that,” I whispered. “If you come, I’ll give you your Christmas bonus early.”

Those turned out to be the magical words. He arrived just a few minutes later in his bathrobe, my knight in fuzzy armor. I smiled because I knew he’d seen worse. Much worse.

“How did this happen?” he asked, peeling back layer after layer of clothing.

“Well, I read that it’s going to be fifty-five degrees tomorrow, so I was trying to grab a sweater from the top shelf when—”

“No,” he cut me off. “Not that. This!”

I craned my neck to see that he was holding in his wide-palmed hands not one, not two, not four, but nine bridesmaid dresses.

“It’s not what it looks like,” I said, worried that his judgment would crush me faster than the contents of my closet. “Trust me, I don’t even like weddings.”

I wasn’t totally lying to him either. When I was a little kid, the idea of my own wedding didn’t take up much real estate in my mind. Whenever I found myself scoring an invitation to a sleepover or to a lunch table in middle school, the girls would giggle over the cuts of their future rings, the colors of their future flowers, and the flavors of their future cakes, while I’d be off in the corner of someone’s bedroom or at the end of a table, crafting paper airplanes from expired love letters I was too afraid to send.

“You hate weddings?” my friend Samantha once asked me incredulously at her sleepover party, every syllable loaded with attitude. I watched as she brushed her Barbie doll’s bleach-blonde hair, her fish-like lips pursed in sour disapproval.

“I don’t hate them,” I said. Hate was a very strong word that my mom put in the same bucket as curse words; I was never allowed to use it. Whenever I had a staring contest with a plate of broccoli or a pile of homework, I would say I “uggghhhed” them instead.

“But don’t you want the flowers and the dress and the giant shiny ring?”

“Not really,” I said, thinking for a second and realizing I had never thought about it before. I was seven years old, and the only thing that regularly crossed my mind was which toy I’d score in my McDonald’s Happy Meal, or how I desperately wished I could sleep through the next lesson in long division.

All the other girls at Samantha’s sleepover talked about how they wanted this flavor cake and that color rose. How their dress would be a cascading waterfall of lace and they’d spend all night twirling around in it. They never mentioned the ooey-gooey love part. They never mentioned the person who would be standing beside them in the photos, at the altar, for the rest of their lives. Maybe that’s because back then, boys still had a major case of cooties.

“Look at her lopsided bangs,” one of the girls said about me as their tittering laughs ricocheted off the walls, hitting me right in the face.

“She’ll never get married,” another girl said as she slid into her Beauty and the Beast sleeping bag.

“You know what I think,” I said, as my cheeks flushed magenta and my voice sounded as if someone was shaking me uncontrollably, though nobody was. “I think if you find your forever person, you two should just do whatever you want.”

At that time, my forever person’s name was Lucas, and we had never spoken more than ten words to each other. Amy was his forever person, and she was sitting across the room from me right now, painting her nails with a coat of glitter and plotting the coordinates of their wedding in some exotic place, like the Amalfi Coast.

I wouldn’t say I was always averse to weddings—more like confused by them. I was three when I went to my first one. I was a junior flower girl, and my diaper matched my dress. My blanket, Mr. Blankenstein, was my plus-one. My mom had to bribe me with a caramel-flavored lollipop to stop sucking my thumb for a couple of minutes so I could use both hands to toss teardrop-shaped rose petals as I tiptoed in my Keds down the aisle.

I remember how the fragrance from the flowers tickled the edges of my nose, and when my uncle said, “I do,” I sneezed so loud that the rabbi had to make my aunt and uncle repeat their promise that they would always stick by each other’s side, no matter whose waistline expanded first.

I remember wondering why I was at a mini-circus, where everyone was drinking liquid that looked a little like pee and wearing fancy outfits that they could hardly move in, even though they had to spend the majority of the night moving around. I remember my dad cutting my food into tiny pieces and I remember sleeping a lot, passed out in my stroller beside someone’s ninety-three-year-old grandpa and a cousin who was slurring his words, which I later learned meant that he was sloshed. Weddings then seemed like fancy schmancy birthday parties where everyone walked around looking like they had a wedgie. I wondered if I’d ever be able to understand the point.

Now I’m twenty-eight, and all of my assets are tied up in bridesmaid dresses. My passport has stamps only from bachelorette party destinations like Cancun and four of the seven Sandals resorts. Every scar on my body is from getting dragged into mosh pits while trying to wrap my arms around a tossed bouquet. I repeat marriage vows in my head the same way people sing lyrics from a catchy song they’ve heard on the radio. And I know never, and I mean never, to let a bride have a Diet Coke before she’s about to walk down the aisle unless it’s through a straw and there’s a blanket splayed over her dress.

“So how did this happen?” the maintenance guy asked me once more, shaking a handful of chiffon.

“All of my friends got married,” I said, miserably.

“Always a bridesmaid,” he said, dropping the dress, grabbing both of my hands, and pulling me up from rock-bottom, sedentary state. “Never the bride.”

He had no idea.

When You Least Expect It chapter one A Familiar Kind of Love
My parents got married when they were twenty-six years old, so on my twenty-sixth birthday, while I was locked in a staring contest with a flotilla of skinny candles on my Carvel Fudgie the Whale cake, my mom asked if she could blow out the final flame that was stubbornly wiggling its fiery wick right in my face.

I agreed, and when it was over, I asked her what she had wished for. She just winked at me repeatedly, as if she had something stuck in her eyelid. She made sure the twinkle of her engagement ring, fused together with her white-gold wedding band, hit me right in the eye.

“I just want you to find a guy who makes you happy,” she said, cutting the cake into three pieces: two miniature slivers for us and one extra-large slice with the most icing on top for my father. “But please, Jennifer,” she went on, “try to do so while I’m still young enough to dance the electric slide with both of my original hips.”

I mentally bristled. There are a lot of guys who make me happy, I thought to myself while running through an inventory of potential prospects.

There was my doorman, who always reminded me to go back upstairs to grab a heavier sweater and a knit hat when the chill in the air began to fog up the windows.

There was the guy who owned the rat-infested pizza shop across the street who always warmed up an extra slice for me, on the house, whenever I dragged my four-inch-stiletto-shod feet (courtesy of the Macy’s clearance rack, of course) into the restaurant—which was usually after a cringe-worthy date. Those dates always ended with me knocking over a mostly full glass of Cabernet Sauvignon onto the guy’s finely pressed Ralph Lauren button-down shirt, or him turning a friendly good-bye hug into an attempt to french my cochlea.

There was even the homeless guy who had built himself a tiny fort out of beat-up Home Depot cardboard boxes and marked his territory outside the Bank of America ATM machine on Third Avenue. He could often be found shaking his Starbucks cup full of change to the tune of a Ying Yang Twins song, and he always remembered to lift up his Yankees’ cap to tell me that I was 57 percent more beautiful when I smiled.

I told my mom she had nothing to worry about as she whispered some ancient-sounding prayer in Hebrew before digging the tines of her silver fork into my birthday cake.

Even before I was in a training bra, and back when I was still on training wheels, I thought I would have absolutely no problem falling in love. I fell a little bit in love with every single person I met, and sometimes I even had trouble letting them go. Literally. The librarian at the after-school day care had to call my mom to pick me up early one evening because I latched onto her calf and wouldn’t stop hugging it after she read us Charlotte’s Web. The same exact thing happened with the mailman, a McDonald’s employee monitoring the ball pit, and Mickey Mouse—all in the same week.

But I truly fell in love for the very first time when I was four years old. He had shaggy, tree-bark-colored hair, and a dresser full of well-fitting OshKosh B’gosh jean shorts. His name was Scott, and his eyes looked like the fabric buttons on Mr. Brown, my teddy bear.

Scott and I were the head of our preschool class’s lines, and we took our job very seriously. We wondered if this was what it felt like to be the president and the first lady. If so, we were ready to take over the universe.

One afternoon, when Mrs. Kay shook us awake after nap time, Scott and I went behind a homemade rocket ship that was set up in the middle of our classroom. We pretended to be astronauts who had just successfully navigated their way to the farthermost spot on Pluto. We took our plastic cups of semifrozen, snack-time apple juice and clinked them together, a quick cheers to all we managed to accomplish before 2:00 p.m.

The next thing I knew, Scott’s pillowy lips were planted smack on the middle of my right cheek. Look at this, I thought to myself. Look how lucky I am to have found love at such a young age, and with such a handsome, motivated, future astronaut!

But right as I went to kiss him back, to let Scott know that I had the same heart-bursting feelings for him that he had for me, he turned to his left and planted his lips on the cheek of some floozy named Melissa. Talk about a mood killer.

That week, Mrs. Kay had taught us the importance of sharing. Rumor around our preschool class was that if we didn’t understand how to do it, if we didn’t give in and hand over our favorite Barbie to our best friend when she came over for a play date, or split our last Oreo when someone asked us nicely during lunchtime, we wouldn’t be allowed to move on to kindergarten. We’d be held back for a year as punishment.

But I knew that love wasn’t meant to be shared the way Scott had shared his precious lips with both me and that mini-bimbo Melissa. I was pretty sure of that.

When a guy finally gave me the undivided attention I longed for, it wasn’t quite what I expected. I was in fourth grade and working overtime to make myself invisible so the other kids wouldn’t make fun of me for being so painfully shy that I couldn’t even utter my own name without breaking into hives and trembles. Jean was a transfer student from Nice, France, the new boy at my private school in the southwest corner of Boca Raton, Florida. He reminded me of someone out of a history book—Napoleon, perhaps. His shoulders always pointed back, his chin up, and his hands remained planted on his hips, as if he were about to make a profound declaration.

On his first day of school, Jean stopped me in the middle of the purple-speckled hallway carpet and asked me which way the bathroom was. I extended my arm to the left, hoping he wouldn’t ask me anything else so I could go back to reading Harry Potter and developing my own invisibility cloak—a fleece sweater draped over my head, where I was determined to hide until it was time to graduate from elementary school.

My slanted bangs, crooked teeth, and dirty white Converse must have made quite the impression on Jean that afternoon, because the next day, during lunch, he planted his feet on top of a sailor-blue plastic chair and straightened to his full height of five-foot-one, ready to make an announcement.

“Listen up,” he said as his prepubescent voice dipped low before hitting a high falsetto, the likes of which I’d never heard before. “I want all of you to know that I, Jean, am in love with Jennifer Glantz.”

I coughed up my pizza bagel onto my orange lunch tray. I prayed that nobody in the lunchroom knew who Jennifer Glantz was. A perpetually shy girl can only dream.

Alas. Three hundred and forty-three pairs of eyes spun in circles until they found a pleasant resting spot on my forehead.

I wondered how well my invisibility cloak worked as I pulled the neckline of my sweater up over my noggin and tucked my legs up into the body of the sweater, hiding everything but my widow’s peak. I closed my eyes tight. Just get through this, I chanted in my head, and then maybe you’ll finally be allowed to transfer to a middle school in some other galaxy.

“I love her so much. I will do anything for her,” he went on. “I’ll even buy her tampons.”

The room broke out into shrills of laughter. People began whooping and clapping their hands together as if they were welcoming Justin Timberlake onto our campus. A wave of “woos!” went through one of my ears and out the other. I hadn’t even gotten my period yet, but now the entire student body thought I was a bleeding monster.

Was love supposed to be as uncomfortable as going to the dentist or, when I finally came of age to experience it, the gynecologist?

I’ll never know why Jean fell in love with me after I pointed him to the bathroom, or why he proclaimed his love like he was conquering a brand-new territory, or why he felt the need to demonstrate the seriousness of his affection by volunteering to buy me tampons. Maybe it was because to Jean, I was a mystery. I was a girl of few words and only slightly more hand gestures, and maybe to him, and only him, that was enough.

By age fourteen, I thought that if I wanted the right guy to like me, I had to make him aware that I liked him by sticking my tongue down his throat. (I don’t know when the girls I went to school with held a town hall meeting and decided that boys no longer had a flaming case of the cooties, but suddenly it was so, and now we had to kiss them. Which they did. All of them. Except for me.)

I would practice a lot in case my moment happened. I’d stand in front of the mirror and slather on some cherry Lip Smacker before placing my lips on the cold reflective glass, moving my tongue in rapid figure eight motions and tiny circles, making out with my own reflection.

When I finally found someone who told someone else he’d be okay with kissing me, I had a mouthful of braces and a deep psychological fear that if the boy also had braces, we’d lock together. Then we’d be rushed to the hospital and my parents would have to see me tangled up in a premarital situation with a guy who was just okay kissing me. They’d probably make him marry me, or at least attend our next Passover seder.

The day I got my braces off, I went to the movies with a group of guys and girls and told myself that before another car flipped over in Fast and Furious 3, my lips would be glued to a guy with the AOL screen name Bucs314. But I waited too long, and right as our chins touched and our lips pressed together, my right leg started to vibrate. My teal beeper was going off in my jeans, which meant one thing and one thing only: the movie was over, and my dad was waiting for me outside.

I wondered, then, if love was all about being in the right place at the right time. The never-been-kissed, fourteen-year-old version of myself deemed that I would probably have to wait forever for it. (Now I wonder if I need to fully dismantle my biological clock, or at least take the batteries out; these days, it’s pulsing harder than a Kesha song right before the beat drops.)

After that ill-fated attempt at romance, with Vin Diesel watching over us, I managed to successfully touch tongues with five people before I met a guy named Ben in college and instantly fell in love. He was the head of Habitat for Humanity at my college and had a pretentious air about him that made him seem as if he was tightrope-walking thirteen stories above everybody else. I melted when he said my name, and I cooed when he repeated world news as if he were taking over Brian Williams’s gig on Nightly News. We kissed for the first time in my dorm room, on the edge of my extra-long twin-sized bed, and by the time he left, I was planning our entire future together. We’d graduate and join the Peace Corps and be the kind of couple who didn’t shower for weeks at a time as we traveled the world, adopting a handful of kids from Third World countries. But one week after our first smooch, he stopped calling. He stopped texting. He stopped responding to me when I sent him emails asking if he’d read the latest National Geographic article on genocide in Rwanda. I was getting ghosted before ghosting had become a thing.

I started to think that maybe love was just a game. A series of passionate, heart-racing hellos followed by radio-silent good-byes. A factory-defective puzzle in which, for me, the all-important middle piece was left out of the box. Other people seemed to have it all figured out, but I was always “losing a turn,” Monopoly style, or shelling out my hard-earned (and decidedly real) money to fund some guy’s steak dinner because he was on student loans and counting the pennies in his sock drawer.

Two years after sticking my diploma in a frame and thirty-six days after landing in New York City with a one-way ticket, I signed up for a JDate account and messaged sixty-five guys before finding one whose bio was made up of complete sentences and not just a series of abbreviations and winky faces. It was my first time on an online dating site, but beggars can’t be choosers—the only guys knocking down my door were of the Seamless deliveryman variety.

When I walked into a Lower East Side wine bar to meet one particular date, I had no idea which guy he was. In front of me was a lineup of freshly shaven gentlemen in gingham button-down shirts, so I went up to each guy, one by one, and asked, “Are you David?” They all shrugged their shoulders and fumbled around with their phones, begging me to move aside so when their internet date walked in, they wouldn’t be caught canoodling with a lost girl with messy blonde hair.

When David finally arrived, I commented that he didn’t look a thing like his profile picture. He was five inches shorter and his hair color wasn’t the same; in fact, he didn’t have any hair at all. But we sat down and ordered two glasses of sauvignon blanc. I rattled off some of the headlines that Matt Lauer had delivered that morning in order to shatter the nervous silence that was beginning to suffocate us.

“Cheers,” he said.

I raised my glass and dinged it against his.

“To what?” I replied.

“You’re just way smarter than you look.” He chuckled and placed his glass back down on the wobbly wooden table.

I told him I wasn’t feeling well. It was winter, and as a Florida native, I wasn’t used to getting frostbite on my exposed flesh every time I left my apartment. I gathered my things to get ready to leave, but when I put my coat on, my left arm got stuck in the sleeve and I knocked down his half-empty—and my half-full—glass of white wine. I watched in slow motion as the glasses shattered and little shards got stuck in the leather upper of his loafers. When the bill came, the restaurant charged us a 15 percent service fee for my performance, and he asked me to pay for the entire bill to cover the embarrassment I had caused him.

I wondered then, at twenty-three, if finding love meant having to share when I didn’t want to, be uncomfortable, and play a game all at the same time. If so, I was already exhausted. I wondered if I had to earn it, like a child earns an extra gold star, like a teenager earns her driver’s license, like a college kid earns her first win at beer pong. But how many times did I have to sit across from a guy while he swished around his half-empty glass of whiskey and yammered on about how he absolutely hated his job in investment banking and couldn’t wait to retire to the sunny isles of Florida? Did I really have to use all of my 60 GB per month AT&T data plan to download sixteen different dating apps to find my Mr. Forever, all while politely smiling whenever someone asked me why I didn’t already have a boyfriend? What did I need to do to find a guy who would eat Doritos Locos on the couch with me?

Now, at twenty-eight, I’m feeling a little more hopeful and a little less constipated about the whole thing. Maybe if I don’t experience these bad dates, these email breakups, these Tinder messages full of bad grammar and lame come-ons, I won’t know true love when it finally comes up to me and gently smacks me across the face.

After all, every person we meet is a plus or a minus to our heart. As I stuck my fingers into a glop of birthday cake icing and drew a faint little heart on my plate, I thought, Maybe it all evens out.

My parents have been married for forty years. I don’t know many things that last that long. My shower curtain needs to be changed at least every seven years. My library card expires every ten years and requires proof of a pulse and a New York City address to get a new one. Even Carnation Instant Nonfat Dry Milk has a shelf life of only thirty-seven years.

My parents met on a blind date back when “I’ll Google you” was something naughty you said after dessert, right before the bill came. My mom had just moved from Queens to Miami Beach. One night, her friend told her to paint her lips magenta and put on a pair of sleek bell-bottom jeans because they were going out on a double blind date.

My dad was visiting Miami Beach from Queens, and his friend told him to shower but not shave, because that night, they were going out with two groovy girls.

That’s the night my dad and my mom met, but funnily enough, they weren’t set up on the blind date with each other—they were matched with the other’s friend. When the date was over, my dad called my mom and said, “I had fun with your friend, but you’re the one I’d like to see again.”

I fear that now, that would translate into a pathetically blasé text, like, “Yo, you wanna hang again without the other two?” I wonder how my mom would respond to that, or if she even would respond to that, if their meet-cute was adapted for modern times.

“How did you know Dad was the one?” I asked my mom after we had eaten our cake and I had peeled birthday candle wax from the dining room table. We both glanced over and watched him sitting on the couch, snoring, the TV buzzing on low volume like a lullaby.

“I didn’t know,” she said, tapping every button on the remote, trying to shut the TV off. “It just felt different yet familiar. A familiar kind of love.”

Maybe, I thought to myself, love doesn’t need to be complicated; maybe it just needs to feel like everything else. Maybe it just needs to feel familiar.

“Lloyd!” my mother yelled as my dad shook himself awake and tried to acclimate himself to his surroundings. There he was, on the soft cream leather couch, his eyes meeting the eyes of the same woman he’d been waking up to for forty years.

“Wake up!” she said. But her voice was filled with patience, and she smiled back at him, as she had so many times before.