Best Of


Look at you—all popular

After experiencing a less-than-ideal social life in his youth, our writer finds his footing with the in-crowd during his first Naples dinner party.

This might come as a shock to some of you, but I wasn’t invited to that many parties as a kid. By either design or decline, I missed a number of social soirees and shindigs that were the talk of the class come Monday morning. I blame the fact that I was in band, a sure poison for popularity among the school-age set. Shout out to all the alto saxophone players in the house—or the doctor’s office or wherever you’re reading this. (And yes, I do think that mole looks suspicious. )

Being a social outcast in your youth leaves a mark. Like men who buy Ferraris or Lamborghinis in an effort to overcompensate for perceived shortcomings, the unpopular youth in many of us longs to get an invitation to sit with an in-crowd. That’s why “Season” in Southwest Florida is such a magical time. 

We all get a do-over. Any of us can transform from ugly ducklings to beautiful swans, because the best parties in this area aren’t based on cliques or favoritism. It’s not about whether you were a cheerleader or a jock. The hosts are merely interested in whether or not you can buy a ticket. 

What a wonderful equalizer 

That simple fact makes life so much easier. And if you’re new to town, you don’t have to hope invitations magically arrive in the mail or wait for a chance encounter with someone in the know. You can just flip through this very issue and find every party worth mentioning taking place between now and the 2020 hurricane season. The next steps involve making a call and writing a check. It’s that easy.

A large part of my professional life has revolved around attending parties, from great New York galas to splashy Hollywood premieres to political fundraisers that fall somewhere in the middle. At this point, my tuxedo has seen more than its fair share of revelry—not to mention debauchery. (If someone can recommend a good dry cleaner, it would be great to get these stains out.) 

When I moved to Southwest Florida, my first local party was for an assignment for this magazine. The opportunity came as a high-ticket auction item from the previous year’s Naples Winter Wine Festival (NWWF). While I’ll avoid names to protect the innocent, I’ll say it was a private concert with a well-known country star held in the private home of a lovely couple who greeted every guest with a smile and a cocktail. I mingled among the smattering of exclusive guests with a hint of New York swagger and a plan to wait until most were on their second cocktail before taking notes in earnest. (That’s how we roll in New York.) Most of the small talk turned out to be unbelievably polite, which I found alarming, but have since accepted. I discovered that a majority of the guests had absolutely no idea who the singer was and just bought the tickets to support the NWWF. It’s hard to find fault in that kind of giving. One particularly lively conversation ended up netting me one of my now-closest friends. She was there on a ticket from a NWWF trustee, who was busy ice racing a Mercedes in the Arctic Circle, as one does. 

When it was time for this country crooner to begin his pre-dinner performance, there was an awkward pause when I was told I didn’t have a seat. After the show, I’d have to experience the rest of the evening from the kitchen. 

Wait. What?

At every other high-ticket party I’d attended as a writer/columnist I was given carte blanche and full access. But here, it seemed, my invite had some fine print. I raised a stink when I spotted an empty seat at every table but was kindly  advised that was reserved for the star to hop around and mingle with guests throughout the dinner. 

The argument was that people paid $20,000 a couple for the privilege of attending this private concert, and how would it look if I just got to attend for free? 

It was a good point. After his set, I was shuffled off into the kitchen. And though I did have flashbacks of not being invited to the head cheerleader’s pool party, I still had a great time and discovered that Southwest Florida knows how to throw a party. 

My point is that you (assuming you’re not a journalist scoring a freebie) will be welcomed at the cool kids’ table. And while you’re  sitting there looking fabulous, you will feel like you’ve arrived. So, get your tickets and let’s party.