I have a love affair with New York City. Since 2001, it has been my travel destination of choice. Now, on my eighth trip to the city, it’s hard to put my finger on what exactly the allure is. All I know is that the most amazing (and sometimes wacky!) occurrences seem to happen when I’m going about my business.

1. Superman Has A Snake In His Duffel

My first trip to New York over Halloween in 2001 was a complete accident. My boyfriend at the time was researching airfare with me (just for fun!) on a website that prompted him for his credit card number. For whatever reason, he entered it and in an instant, the tickets were booked with no refund allowed.

We had no real plans for our last-minute trip (and the city was still reeling from 9/11) so we headed over to my friend Voltaire’s deejay night in the East Village at a fetish-themed French restaurant (?!)

Halfway through the night, a black man with blue contacts and a full Superman costume (complete with pumped up faux muscles and big, red boots) entered the bar area with a duffel bag, calmly unzipped it, and pulled out a MASSIVE snake. He nonchalantly wrapped it around his neck and later, thrust it towards me, telling me to hold it. No way! Not then, not now, not ever.

Lesson learned: When in New York, always expect the unexpected.

2. The Roasted Pig & Secret Passageway

During a stay in the city in 2003, my friend invited me to a house party in the West Village. Her good friend was dating a much older man from Berlin who happened to own a quirky townhouse. As we walked towards the front steps, a group of well-heeled (and well preserved) Europeans were gathered outside near the stoop, putting the finishing touches on a roasted pig.

Inside, there was a spread of baguettes, brie, and of course, the roasted pig as the centerpiece (complete with an apple in its mouth). I felt out of place in a red cross hoodie and pointy boots, but everyone was extremely gracious.

Things began to feel surreal when my friend disappeared into the bathroom for what felt like an eternity. She’d noticed a mysterious stream of light coming through a seam in the wall. Upon further prodding, we realized that it was a secret passageway to the living room, complete with a bookcase on the other side, just like you’d witness in the movies.

Walking into the living room on the other side of the wall, there was a mattress with a sculpture made out of clothing tags hanging from the ceiling directly above it. I went back into the kitchen and pretended to devour a pig leg:

As we walked back into the night, one of the perfectly refined women from the party chased after me, asking me where I’d gotten my hoodie. And, that is one of my favorite things about New York; the seamless meshing of people from all different walks of life.

Lesson Learned: When in New York, always be yourself no matter the crowd or class of your company.

3. From the Trenches to the Trump Plaza

Six years ago, I had my mind set on attending F.I.T. Staying with a friend on the Lower East Side and taking the subway by myself, I got lost in Midtown on my way to an orientation. I finally found my way to the school and at the end of the presentation, walked over to an administrator to ask some more questions. We chatted briefly and I mentioned that I was visiting from Oregon.

A mom and daughter overheard me and said that they, too were from Oregon. They graciously invited me to spend the rest of the day shopping with them around Times Square. When it was around dinner time, they invited me back to their friend’s penthouse apartment at the Trump Plaza. I was astounded that they brought a complete stranger back to meet their family; the view from the 52nd floor of Central Park was amazing!

We all went out to dinner at a restaurant with live opera and hung out like one big, happy family. As I caught a cab the 100 blocks back to my much more modest digs, I realized that anything in the city really is possible and most of it hinges on chance meetings.

Lesson learned: Get out, make small talk, and always believe in the kindness of strangers! From there, anything can happen.

4. Boy George & ‘Giving Back’

Back in 2005, I had way too much free time on my hands. Besides some minor freelance jobs, I was lucky enough to have two full months in the city with very little planned. When Voltaire invited me to see Boy George deejay at a club night called Charm School, I immediately jumped at the chance.

Yes, Boy George was amazing, but even more so was the transvestite sitting next to us. Seems that she knew Voltaire from a past job and was not only completely out of her mind, but also brimming with amazing stories! At one point, she described in graphic detail about how she performed sexual favors for top CEOs and then donated her earnings to charities in New York. She explained that it was her way of ‘giving back’ to the community! Totally surreal.

Lesson learned: Always drink way less than the company you’re keeping so you can remember their stories the next day!

5. The Filthy Schoolgirl

In the spring of 2005, my friend Bianca had just landed a cover job for an album called ‘The Filthy Schoolgirls’ and asked me to be the model.

We spent an afternoon trolling school uniform stores in Brooklyn, searching for the perfect accouterments on a tiny budget and arrived on set at Pratt University.

From that moment on, I really did become a filthy schoolgirl. My face and outfit were smeared with charcoal until I looked like I’d been playing in a coal mine.

Once the shoot ended, my goal was to race to the bathroom and quickly clean myself up so people didn’t get freaked out and that think I’d been beaten up. As I skipped down the hall, my plans were foiled when a huge pack of Japanese tourists crossed my path. They stared but didn’t dare mutter a word.

In the bathroom, the charcoal didn’t come off so easily and I was forced to take a jaunt with Bianca through Brooklyn, all smudged and shivering, sipping a carton of orange juice. The results were worth it; I not only got the cover, but a big fold-out poster inside the CD case!

Lesson learned: Treat every opportunity as an adventure and it will make your life all the more richer.

Thanks for reading about my adventures in the Big Apple! Is there something amazing that’s happened to you in the city that you’d like to share? Stories, please!