Dating : The Boyfriend Guild

I wonder. Is there a Boyfriend Guild, a centuries-old band of merry lovemakers and heartbreakers? Perhaps they gather for an annual conference in a swanky beach hotel or a rustic cabin in the foothills. Maybe they have a creed and membership dues and an obscure Instagram account. What I am certain of is this: Each member of the Boyfriend Guild is marked with a destiny, a distinct duty they must fulfill in humanity’s never-ending drama of love giveth and love taketh away.

The First Boyfriend

Most often, the first boyfriend lives in the land of awkward, trying to figure out puberty and trying to appear cool as he adjusts his oversized prescription glasses. Few, very few, first boyfriends sustain this destiny because they are boys turning into young men and they think girls are supposed to be gross but the peer pressure to have a girlfriend is worse than the cafeteria food. So, he begins his quest with a shy glance as you pass in the hall and then the next week, he sits one seat closer to you in math class. It isn’t long before the two of you are holding hands as you stroll through the county fair, begging the two hours your parents gave you to never, never end so you can share a gooey bag of cotton candy and sneak behind the water gun game to steal what the two of you were certain was a real kiss.

My first boyfriend would save us a seat on the school bus, and we would flirt and laugh and bump our shoulders together. He was smart; a far better student than I was. I don’t think his mother approved of me; on account of the sneers she would shoot at me across the crowded auditorium during school plays. I was twelve and outwardly quirky and more of a tomboy than a girl. Maybe she thought he could do better.

The High School Sweetheart

He is the one that wedged that folded love note into the vent at the top of your locker. His sister helped him write it and he blushed when he read it. He smiled when he imagined your smile as you unfolded the note in the quiet corner of the library. He’s the one you fooled around with on the couch, only after you were certain your parents were asleep, and only after he gave you his class ring to wear. He was the star on the basketball team and the football team, and you would melt into his warm chest when he wrapped his strong arms around you. He sheepishly struggled with pinning the corsage on your strapless prom dress until your mom saved him from breaching the forbidden zone of your boobs.

I believed my high school sweetheart was the love of my life, the one I would marry and have babies with as we skipped through a life of messy minivans and middle-age Sunday snuggles. We’d buy a house in our small country town and host backyard barbeques and help his parents with their yard sale every spring. His smile was crooked; but like everything about him, it was perfect to my sixteen-year-old self.

The Boyfriend You’ll Never Have

You sit perched on a stool, your back and elbows against the sticky bar. The throngs of people and the thumping music cannot distract you from starring. He’s on the far side of the room, talking to a few of his friends. He is tall and beautiful and, in your mind, you write the dreamy romance the two of you will share. You dare not blink lest he disappear in a poof. Competitors surround you so you sit up straight and bolden your stare. You imagine him approaching you, in slow motion, his sway and swagger as sexy as his deep brown eyes. And of course, he’s a gentleman and he’s destined for career greatness and yes, of course, he has a puppy that is almost as cute as he is.

I can still picture the one I will never have. I used to sneak behind the fieldhouse and watch him run sprints on the track, his leg muscles stretching and straining in the bright afternoon sun. I would find any and every excuse to frequent the bookstore where he worked part-time, and more than once, mustered enough courage to exchange casual words with him. I knew I was one of many who yearned for his attention as I circled around his life, clinging to unquieted hope.

The Boyfriend That Wouldn’t Go Away

A pitiful, searching soul, the boyfriend that wouldn’t go away can still haunt you went you least expect it. After the painful breakup, he worked his way into the outer fringes of your life as it continued without him, connecting with friends of your friends, and somehow appearing at the same happy hour as you. This boyfriend couldn’t abandon the blooming, beautiful love the two of you had at the beginning and he waited, as if at a vigil, for the spark to rekindle. Years later, he left you voice messages around the holidays or your birthday, just to say “Hi”, his quivering voice filled with faraway yet not-forgotten memories.

I tried to be sympathetic when the boyfriend I broke up visited me unexpectedly. His face was red and raw from crying and there he sat, shoulders slumped, with a shoebox full of photos and movie stubs and vacation mementos. I felt as terrible as he looked. My words of encouragement didn’t work. Neither did calling his mom two weeks later to ask how he was doing. Maybe she thought I was the one for him.

The One That Got Away

The boyfriend that got away is the one you treated like crap because you were living large in your early twenties and far more interested in the social limelight and pulling pranks in the college dorm. He adored you. His parents adored you. Your parents adored him. He would save his money to take you to fancy restaurants and you loved how his skin smelled after he showered. But you were also cocky and convinced there were better fish in the sea. He tolerated you, convinced you would settle down and come to your senses. You didn’t. You broke his heart without a second thought. He’s the boyfriend that steps in and out of your memories, the one that whispers, “What if…?” in the silence of a sleepless night. He is in the tears that come when you are sad, when you accept there are fewer years ahead of you than behind you.

Maybe I should have listened to my best friend back then. She loved that he loved me, and she saw us as forever together. Decades later, she still weaves him into our random conversations, a gentle reminder of what I left behind, what might have been. He is the one I will search for in the next life.