I make fun of myself often, telling my friends I’m like Pavlov’s ‘ramp tramp‘. I am classically conditioned that when I hear the sound of a skateboard wheel hitting the pavement, I immediately salivate – it’s as though I am intrinsically inclined to jerk my head and be on high alert for the big reveal – who is it riding this board? Is he cute? Will he speak to me? Am I going to have to pay for his brunch?

I blame my obsession with man-boys on being sandwiched in between two brothers – my older brother six years my senior, was always a skateboarder or a BMX rider – ‘extreme sports’, by their very definition, were the pinnacle of masculinity to me. My younger brother, also a skater, was always editing skate videos to songs by The Cramps and Tribe Called Quest. My pre-teens were spent jumping on the trampoline in our backyard so I can get just enough of a peep above the fence to perv on my brothers’ herd of teenaged male friends in Cuban chain necklaces, studded ear piercings, wife beaters (what is the now-PC version of this coin of phrase? LMK), skate decks with misogynist imagery or hilarious onamatapoeic sayings, or words like “SHAKE JUNT” or “CHICKEN WINGS!” sprawled across the bottom. A personal favourite was a cartoon mock-up of a 2007 bald, angry Britney. Swoon.

Yet, in my mid-twenties, I still somehow gravitate towards this stylized way of being when it comes to my personal or romantic preferences. I myself was one to wear my messy trainers even in the chicest of Condé Nast offices, and to this day I fawn after a man in London skateboarding in his tweed suit, briefcase in hand – a very rare occurence, but an occurence, nonetheless. It seems like I couldn’t find the boy I wanted, so, somehow, I tried to become him. I went to music festivals and sat on the pavement drinking Red Stripe. In my adult life, working in fashion always gave me a chance to find references, build and image, and create something people wanted. Something that I found desirable.

I always pictured my first love/relationship/dalliance being with an emotional skater who wanted nothing but to spend all of his time with me listening to old vinyls when he wasn’t at the skate park. Who knows – maybe he had a passion for black and white photography in his spare time, a girl could dream. My musical tastes in middle school and highschool, now, seem like a subconscious attempt to search for my tribe at an Animal Collective concert, or find The One at that free Sonic Youth gig in Williamsburg.

Needless to say, it clearly never happened. I spent my early twenties looking for security. The first (and only) real relationship I was ever in was with an introverted professional who lived in a nice area, wore nice suits, and worked at a law firm. It was a teenage kind of love, that all-encompassing, I-can’t-live-without-you, let’s text all day, OMG I LOVE YOU! kind of love that gave me butterflies when he called, where you can’t help but turn red when he was brought up in conversation, and finally, of course, a fleeting love we should experience at least once, if we’re lucky. I found myself straying away from what became a healthy companionship because I craved that silly, messy, fun, young, teenage love.

For two years now I feel like dating has become less of an experience for me and more of a social experiement. These nighttime interviews involving wine (but mostly tequila shots) have done nothing but bring out the investigative journalist in me – I find myself now collecting experiences, stories, friendships, and personalities I’ve uncovered in the dating realm to add to my personal experience and my dossier of entertaining pub fodder I would share with friends.

These dates I go on – somewhere upwards of thirty to be exact, if I’m counting, have rarely involved a connection and more often than not left me yearning for that butterflies-in-your-stomach, ‘let’s make out in the rain’ kind of feeling I never truly got to match with the detailed narrative I’ve been mapping out in my head for so many years.

The sparse connections that I have made were really just men who ticked the boxes of the boys I had always fawned after. I find myself in a dating scene limbo, too afraid to move forward as I never feel the butterflies, so what is the point of making another attempt to meet? I take these dates and use them as opportunities to build long-lasting, platonic friendships with the man at hand, perhaps replacing the older brother that wouldn’t let me in his room when he and his friends were changing skate trucks, or my adult-version of the intimidating group of boys I’d ogle at the check out desk at Vans Off The Wall when I was thirteen, buying slip ons with my babysitting money.

When my friends call and ask about my dating updates, or request guy advice, I find that I can’t give any when it comes to living out a perfectly adult, respectable, equal relationship. To me, at this space in time, men fall into two categories.

1. A friend I have for life, where we tag eachother in memes and talk about music or
2. Someone who doesn’t exist yet – that all-encompassing, let’s get married and have babies imaginary guy on a skateboard, who only sees me.

That mature, companionship thing? No idea. As I sit cross-legged on my bed avoiding deadlines and human interaction, with my phone on airplane mode… I don’t think I’m ready for that yet. Friends are getting engaged, married, having babies, finding romance and stability while I refresh my dating apps. Dating is exhausting.