This is a story about the biggest mistake I’ve ever made.

Summer of 2002 – May, to be more exact (I’m glad I keep weird notes to myself for my much older self to discover) – I had just started performing comedy. Not a lot, mind you. Maybe one gig a month, at best. I was working at a fetish porn company as a web designer. I was in the longest relationship of my life to that date (at that time, it was about 8 months – but it would go on to be 3+ years long). I wanted to live in New York City, as a comedian and web designer. I knew this was a difficult task, and it would take a great deal of preparation.

As luck would have it, my boss at the porn company knew the owner of a huge (at the time) porn company out in Florida. He said they’d been looking for someone for awhile, and were open to working remotely with the right candidate, but they preferred to have someone in-house for the first few months. After doing some research, I discovered that rent prices in FL are ridiculously cheap, compared to both CA and NY. To this day, I can still find 1-bedroom places in walking distance to the beach for around $800/month (back then, they were around $550/month) . In addition, FL seems to be the only place in the world that regularly offers 6-month leases.

The plan was simple :

1. Move to Florida
2. Work at the porn company (which was offering almost double what I made)
3. Save up money by living in a cheap apartment (which was about half of what I was paying)
4. Move to NYC with all that money I saved¹

My girlfriend at the time – let’s call her… Cathy? No, wait, she was latina, so … hmm.. fuck it. Her name was Celina. We both had LiveJournals at the time and blogged about everything, so no reason to hide her real name now. Celina thought I was a fucking idiot. Now, mind you, I had told her around the time we met that I was hoping to move to NYC at some point in the next year — long before I’d considered doing comedy, mind you — so I excused actually going through with this plan as “she knew what this was”. Naturally, when we met, I didn’t have a solid plan that would get me to NYC so it probably sounded like one of those grandiose things dudes in their early-20s talk about doing but never actually end up doing . But, now, I had a plan. She wasn’t exactly happy about that.

I talked to the porn company guy (let’s call him “Porno Joe” for this story) and he said he had a spot waiting for me on his team, and to call him when I was “all settled in”. I quit my current job and went freelance. At the time, they needed thousands of photos manipulated for an upcoming “Huge Cocks” website. Over the course of a month, I edited 2000 photos. At $2 per photo, my Florida fund was pretty well handled. The nightmares I had about being attacked by giant dicks, where my own dick was 1/10th its normal size, subsided in time.

I looked around online for an apartment – finding that Ft Lauderdale was a hop, skip, and jump from Miami but about 20% cheaper – and found one in a good area, at a good price. When I called, they told me there was a huge grocery store on the corner nearby, the area was lush with greenery, and the neighborhood was safe and clean. I did a check-by-phone for the deposit and set about finding a cross-country moving company.

About 2 weeks prior to the move, I dropped into a dive bar where some friends were performing. They were short a comedian, and asked if I wanted to do 10 minutes in the Feature spot (one before the Headliner). At the time, I’d only ever done 7, but I got up and somehow made it work. It was a fun show. What I didn’t know is that the comic onstage after me was doing a showcase for some comedy agents. After the show, one of those agents talked to me for a bit – I thought he was just some dude at the bar – and he was shocked when I said that was only my 4th time doing comedy. He said “well, I’d love to get you on some more shows, and work with you to get bigger gigs”, and handed me his card. My response, which I’ll regret for the rest of my life, was “ahh.. listen, I’m moving to Florida in 2 weeks. I appreciate the offer though”. He was shocked. Confused. “Why are you moving to FLORIDA of all places?” — I explained my whole plan, and he just nodded along, occasionally rolling his eyes, eventually saying “Listen… you’re in California. You know comics here. I’m offering you more gigs out here. Don’t go to Florida, man. And New York? Jesus, that’s a shark tank for comics. Are you sure about this?”. I was sure. He said I should take his card anyway, in case I change my mind.

You’re allowed to yell at your screen : I didn’t even take his card.

The moving company came a few days before I left and loaded everything I owned — except for my cat, my laptop, my backpack, and my video camera — into a series of warddrobe boxes. There was no turning back now. Everything in my life was on its way to Florida. I spent some time on dating sites, looking for a girl in Florida that wanted to pick up a complete stranger from the airport and drive him to a hotel room. Surprisingly, I found one, and she was even looking forward to showing me around.

When I got to the airport, the flight was delayed. I found this out while waiting in line to check-in, and Vanilla fucking Ice was yelling at the counter lady about “I need to get home today!” and she assured him that it was only a temporary delay. I’ll never forget walking down the aisle on my way to my seat, passing by Vanilla fucking Ice to sit. I should’ve taken that as an omen. Wherever Vanilla Ice is going, you probably shouldn’t join him.

When I arrived, my internet date was there to pick me up. I recall almost nothing about what she looked like, but I wasn’t particularly attracted to her and we didn’t really “click” (and I didn’t really care to try). She brought me to my hotel, even hung out in there for a bit, and then took off. Saying I should call her sometime if I wanted to hang out.

I laid down on the hotel bed, cuddled up with Bouschka, and fell asleep almost immediately. I had a big day ahead of me.

²

1. Step 5 : Profit ↩

2. header photo credit : Olin Gilbert ↩