Why I Always Talk to Strangers on Planes

Some people consider their in-flight time as a time to catch up on work, to finally watch movies and TV shows they’ve been queuing in their mental “must watch” list, or to finally get a few hours of uninterrupted sleep without phone calls, text messages, or meetings rudely killing their chi levels.  Although I try to accomplish all of the things in even the shortest flights, I always manage doing what I do best: becoming best friends with complete strangers that are sitting next to me.
You may have already read the story of how the woman in seat 7B changed my life, but now even two years after that, I still manage to meet the most interesting people on planes. This story is the perfect example.
Last month, I was invited to be a guest speaker at GenYOUth’s summit in Dallas, Texas as an “inspiration mentor.” The role required me to lead sessions that would help the young entrepreneurs at the summit. The talks varied from touching on values, perseverance, and basically how to master the art of being a boss a$$ b*tch.
The flight from LaGuardia to Dallas-Fort Worth is where the story really begins. I board an early morning flight out West, and to mentally prepare for the series of speeches I was going to give in Dallas over the course of the next few days, I decided the plane would be Zen mode. For once, I didn’t feel like making small talk with anyone near me, so I put in my headphones, sunglasses (like a diva) and attempted sleep for the three airborne hours.

plane diva
I was in the aisle seat, next to me was an adorable elderly Asian woman, and in the window seat was a woman in her mid-40s who had my same skin complexion. Somewhere over Philly, the two strangers became girlfriends. I smiled because I know the feeling of sitting next to someone on a plane that could change your life. I didn’t even consider that it might happen to me on that same flight. I wake up with about 50 minutes left until landing. The flight attendants were passing out sips of free soda, and offering paid snacks. Like always, I shrug my shoulders and planned on starving until landing because who’s tryna pay $12 for some cashews? Not me boo boo. Then I felt a nudge from the lady sitting in the window seat. I see her mouth moving so I take out a headphone as she yells over the crappy in-flight acoustics,
“Sweetie, get something, it’s on me please,” in her Jamaican accent.
“No thanks, I’m ok.” 
“No darling, I work for American Airlines, it’s free. Get whatever you want.”
It was as though I was so caught off guard by free food on an American Airlines flight that I forgot my insane hunger.
“Ok, can I have some assorted peanuts please?”
Meanwhile, the Asian lady ordered a gourmet chicken Caesar salad. Clearly, she knew what was up.
I start chomping on the peanuts and just slightly turn down my music to thank the stranger who had fed me.
“Thank you so much, really, you didn’t have to.”
The Asian lady looks at me to break my sappiness,
“Oh, you so pretty! I’ve been wondering if your hair was real this whole flight.”
I let her touch my hair and laughed because so many people have the same curiosity. We talk about hair products, and one thing leads to the next,
“Do you have a boyfriend,” asks the tan lady in the window seat.
“No, no I’m single.”
 “Good, girl, stay away from boys, they give you headache, heartache, and infection,“ while motioning to her head, her heart, and her crotch. The Asian lady started nodding her head and laughing like a little girl to agree with this statement.
That’s when I lost my $hit and instantly fell in love with these two older women who had so much spunk they almost put the dynamic Damon & Jo to shame.
I introduced myself and got to know Marla, the 43-year old Jamaican woman in the window seat, and Linda, the 65-year old Filipino woman who had the energy of a 22-year old.
They drew me into their conversation that bounced around from them working at an airline, to planning a trip for all three of us to go to Jamaica, Brazil, and the Philippines, and finally we get to the subject of what I do for a living.  The dreaded subject that’s still hard to explain despite me having pitched it probably over 1000 times. I explained Shut Up And Go as best as I could, and mentioned the struggle of having to convince these networks and huge companies to invest in us. Marla looks at me and says,
“Honey, why don’t you give my friend Stevie a call. He loves helping out youngsters. You know, Stevie Wonder.” 
Umm… excuse me, THE Stevie Wonder? Yes. That’s exactly what she meant.
Here, take down his number. As a matter of fact, call his wife too.”
And that’s when I bagged Stevie Wonder’s private number. I thought it was a lie too, you never know if these people play a different character on every flight they get on,  ya know? But when I got to the hotel room, I called the number and here’s what happened:
Stevie’s Private Number Recording
Linda on the other hand had been a millionaire twice with her handbag manufacturing company. Back in the day she produced for Gucci and Prada among other huge designers. Of course, she didn’t tell me any of this, she’s far too wise and humble for that. Her grandson told me on the low when we arrived at the DFW airport.
It’s been months since the airplane shenanigans and I still get phone calls from both of them regularly to see how I’m doing.  Marla’s connecting me to Stevie, and Linda’s working on connecting me to her investor contacts. Beyond what they’ve been offering me, it’s just one of those things that make you put your hand on your forehead and think,
damn, if I wouldn’t have been at that place at that time, willing to make a conversation, none of this would’ve ever happened.”
strangers on planes
PS: I’ll keep you posted on what happens to the Stevie Wonder pitch because clearly I chickened out the first time around ;).
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