Me and my mom flying first class on United in 1999

I’ve been very fortunate to have flown countless times and to learn from an early age that you can fly both comfortably and cheaply if you take the time to learn some of the tricks. That’s actually why I created my newsletter and website in the first place, in 1995.

Back then, it was much easier to fly first class. Heck, some people got upgraded just by dressing well, being nice or flashing a travel agent card. (Of course, dressing well will no longer get you upgraded, despite some publications’ insistence that it will; here’s how you can really get upgraded.) Times have changed with the introduction of high-tech computer systems but I’m still able to fly first class even on a budget. If you’re interested in learning more tricks, you can sign up to receive my free daily travel tip.

Anyhow, this post is about the people you meet on airplanes and specifically, one person I had the great pleasure of encountering.

One thing that’s nice about traveling solo is you never know who you will be sitting next to. I know … it’s also the downside, especially during COVID. But over the years, I’ve sat next to far more cool people than I have jerks. In fact, I’ve only sat next to a couple of not-very-nice people and I know that some people just don’t like to talk to their seatmates. If I have a lot of work to do, I’m one of them.

But pre-pandemic, I used to have some of the best conversations and meet all kinds of extraordinary people from all over the world and walks of life while 35,000 feet up. The most exciting were celebrities. When I used to fly between Los Angeles (LAX) and New York (JFK) every other weekend for three years when my mom was sick with cancer, I saw and even sat next to many of them. Here’s a fun post with tips for increasing your chances of sitting next to a celebrity on a plane.

One of the best conversations I ever had was with Joanna Shimkus Poitier, Sidney Poitier’s wife. I just reminisced about it with my wife after learning the sad news that Mr. Poitier just passed away. I had no idea who she was and I’m more ashamed to say that at the time, I didn’t know of her husband. I know, I know … I didn’t watch many movies and the ones I did watch weren’t exactly high-caliber. I was in my twenties and this was in the late 90s.

We were on a United Airlines flight between LAX and JFK. I got upgraded to seat 2A and Joanna was in 2B. I can guarantee you she paid at least 10 times for her seat because I used to fly round-trip for under $300. But because back then, I used to know most of the crew, had top-tier elite status and brought chocolates for the crew, they used to treat me like a celebrity.

I think this is how we got started talking. The flight attendant came around to take food orders and Joanna said she would like … The flight attendant cut her off mid-sentence and said, “I’m sorry, I’m just taking the orders of our elite frequent fliers and then I will start from the front to back.” There were only two rows of first class and often times by row two, passengers would be out of luck for the most popular dish – usually the chicken.

I was thoroughly embarrassed and felt it wasn’t right, especially since I’d gotten a free (double) upgrade. So, I said, “I’ll have whatever my seatmate is having,” just to make sure she got her first choice. Joanna was very appreciative and inquisitive of who I was and we ended up talking for most of the five-hour flight.

Before disembarking, I recommended a Thai restaurant for her and her husband to go to that night on the Upper West Side, which I know they went to because she later sent me a thank you note.

When she found out that my mom was sick, she either gave me a copy of Sidney Poitier’s book or sent my mom an autographed copy (the details are fuzzy all these years later). All I know is that my mom was thrilled to receive the book and shocked that I didn’t know one of the silver screen’s most famous actors.

Just in case Joanna is reading this, please know that I am sending you my most heartfelt condolences. I know there are plenty of people up in Heaven who are going to welcome and look after your husband, my mom included.

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