My Weird, Fun, Life-Changing Quest to Have Sex with 100 Different People

GUILLE FAINGOLDSTOCKSY

A few years ago, I uprooted my entire life on a mission to find happiness.

I had just quit a 15-year career in tech startups, moved across the country to New York, and enrolled in art school full-time. I went from spending my days (and nights) taking international conference calls and building other people's businesses to reading poetry—and building stories of my own. Serendipitously, my sweet boyfriend, James, also had a great job opportunity in New York, so we moved east together.

Outwardly, everything seemed perfect: a 47th floor apartment near Central Park with a doorman, a dog, and a beautiful man.

But one day, staring at the cardboard boxes we'd never unpacked, I realized I still wasn't happy.

I've always been a vocal feminist and a proper #GirlBoss—before it was even a thing. But in my personal life, I've had a long history of putting myself second. Moving in with James, despite my deep reservations, was only the latest example. Before him, in a different relationship, I'd ignored our sexual incompatibility—and in turn my own pleasure. I found myself unsatisfied, depressed, and 30 pounds heavier.

"I wanted to understand who I was sexually when I wasn't saddled with labels like 'girlfriend' or 'prospective wife.'

The pattern was clear: I was unable to articulate my needs in a committed relationship.

With James, I'd once again come to a place where I couldn't recognize myself. We'd essentially become roommates who never had sex anymore. We decided to separate.

Cut to a couple years later. I was still not quite ready for a long-term relationshipbut I was tired of going without—I wanted to explore sex again. And I wanted to do it with as many different people as I could without letting myself default to the familiar trap of monogamy. More to the point, I wanted to explore who I was with radically different people. And I knew I would have to go big.

So, in the same way that adventurers set off to backpack across Europe before turning 30 or climb Mount Everest before they die, I set a goal to have sex with 100 partners before my 40th birthday. Along the way, I would aim to regain control of my own happiness, and reconnect with my fleeting orgasms—I wanted to understand who I was sexually when I wasn't saddled with labels like "girlfriend" or "prospective wife."

Before we begin...

3 Things to Know About my Sexual History:

• My 20s were a blur of transactional hookups thanks to working insane hours in tech startups. Sex was an escape in between meetings and red-eyes.
• I didn't have my first orgasm until I was 31, in a committed relationship, with someone who took his time to truly discover my body.
• James was #57.

The Rules:

1. Repeats don't count.
2. Oral sex doesn't count. (More on this later.)
3. I would have to orgasm. I would never compromise on this again.

And with that, I signed up for a slew of online dating sites and was on my way.