**The following post is part of a much longer piece about my 2014 trip to Italy. It will be a 3 or 4 part series so stay tuned!**

It wasn’t until that girl was wrist-deep into my shorts that I even realized I was being pickpocketed. It was nothing like Ocean’s 11 or any of those hijinks movies. A slick dude in dark, non-descript clothing innocently bumps into you on the street. Maybe he even apologizes. An hour later you try paying for your triple Americano only to realize you’ve been had and your wallet is now that dude’s property. I was prepared for that dude. As a lifelong city dweller I guess a part of me is always prepared for that dude. And, honestly, I thought I was prepared for gypsies too. In hindsight, I realize I was prepared for Esmeralda (Disney version). Certainly I was savvy enough to spot a flowy top and tambourine in time to dodge out of the way. However, it wasn’t Esmeralda (Disney version) who currently had her fist in my pocket. Instead, it was a 19-year-old girl in jeans and a t-shirt that could have easily passed as American, who had a tight grasp on my passport, my phone, and my future.

In that moment time stopped. My mind went into slow motion and played back for me a scene from seven days earlier. In my mind’s eye I could see Andrea splayed out spread eagle on the floor of Newark International Terminal as she dug through her carry-on. My flight from Los Angeles landed 20 minutes earlier so both my phone and my brain were still on airplane mode. The sight of Andrea’s luggage excavation left me mesmerized, Marnie too. Who knew an innocuous canvas tote could hold so many necessities. Envelopes, folders, itineraries, travel sized toiletries, actual toilet paper, and resealable bags (that often contained more resealable bags) were organized in a labyrinth-like fashion inside this vortex of a carry-on. Andrea’s hands were focused on their mission but her tone was jovially conversational.

“We definitely need to be careful of gypsies…especially in Rome,” she absent-mindedly declared. Andrea’s decades in publishing meant she was a seasoned world traveller and spent a fair amount of time in Italy. I, on the other hand, was a Midwestern boy turned Southerner turned Angeleno, who had never been outside of the good ol’ U.S. of A. I took note of the advice but my mind was focused more on the half-eaten sandwich she was trying to unearth from her bag. Those peanuts I inhaled while on my 5-hour journey from L.A. weren’t going to hold me over for much longer and we were minutes away from boarding a 9-hour direct flight to Rome. Julian’s suggestion of “airport sushi” was vetoed due to time constraints. Half-eaten pastrami and swiss would have to suffice.

“Got ‘em!” Andrea proclaimed as she tossed the sandwich to me and threw a small bag to Marnie. I immediately got to work on the questionably aged hoagie while Marnie opened her bag to discover four medieval anti-pickpocket fanny packs.

“Really mom? Do we need these in the airport?” Marnie questioned.

“No but I have one for each of us and you should take it now,” Andrea said. While she demonstrates how to attach the contraption (“right under the boobs”), she relays to us the story of how an Italian woman once came charging at her with a pair of scissors to physically cut the purse off of her shoulder. Andrea had been walking with a gaggle of Redemptorist priests (as one does) down a crowded Roman street when it happened. The priests instinctively encircled Andrea and shooed the scissor-wielding gypsy woman away. As I scarfed down the last bite of slightly soggy sandwich, I couldn’t help but picture Esmeralda with a tambourine in one hand and scissors in the other, a conspicuous threat to say the least.

So with my post-sandwich blood sugar back to a healthy level and a fanny pack chaffing my stomach (“right under the boobs”), the four of us got in line to board the plane that would take us on a 10 day, multi-city, Italian adventure of a lifetime.

As is all too common, this wildly ambitious international vacation originally started out as a weekend getaway to a winery in Missouri. Marnie was a few months away from graduating with her master’s degree. The process had been a long one so it seemed like an occasion worth commemorating. Stomping some grapes and getting drunk in the rolling hills of Missouri looked like the most appropriate way to do that.

Marnie is the best friend who I’ve known since the literal first day of my life. Somewhere in the ethos, there exists a picture of a 3-year-old Marnie holding a days-old me while sitting on my parents’ heinous mud brown 1980’s couch. I was a big baby (still am) and the two of us are almost the same size. It’s both comical and shocking. Ever since that moment, we’ve been some variation of roommate/neighbor/travel companion/source of frustration/confidant/friend.

Months before she was set to walk across the stage to get her diploma, I emailed Marnie’s parents to see if they were planning anything. In the absence of husbands/boyfriends/lovers, duties like that tend to fall on the gay best friend. I almost always oblige. Julian and Andrea were basically co-parents alongside my parents when I was growing up and it was only natural that they be my co-conspirators in planning the graduation celebration.

Nothing was on the books yet so the three of us began brainstorming. Should I come to St. Louis? Should we meet up in Chicago? Surprise her or no? I had only been in L.A. for 7 months but was desperately ready to get out of the city. I figured I would fly to St. Louis and we’d go from there. It would probably end up being a fun but casual party. Somebody threw out the idea of a winery an hour outside the city. An overnight getaway in a lodge out in nature. Alcohol under the guise of culture? Sign me up. Schedules were cleared and excitement started brewing. We eventually let Marnie in on our plan.

I procrastinated long and hard on buying my plane ticket. This is a perpetual bad habit of mine but, in some cases, it ends up working in my favor. Out of nowhere I get an email from Andrea: “Don’t buy flight to STL. I just got word that my mother passed away. How do you feel about going to Italy instead of winery in MO?”

Um, I think I feel pretty good about that.

***