Posted on 2020.09.07

It was so amazing to FINALLY get away. Private flight to an exclusive resort? I’m spoiled now; I don’t think I can ever fly commercial again.

When he called to book me as a Travel Companion, I was a little surprised. We had gone on quite a few dates last year and even though they were all amazing dates, he didn’t strike me as the adventurous type. Even though my profile listed me as a Travel Companion, and he traveled often for work, he never mentioned taking anyone with him. Even when his work took him to some of my favourite destinations and I made the connection, he never suggested we go together. I assumed that he was a workaholic and wouldn’t have time for a Companion while he was away. Then, one day I got the call that he wanted to take me on vacation with him. Vacation? With a beach? Exclusive resort?

Count. Me. In.

I didn’t realize it was a private flight until the confirmation was sent over. Considering what he did for a living, it made sense to fly private. But this would be my first time. While I was never the type to dress sloppy on a flight, I knew I would have to step my game up for this one.

One of the benefits of flying private? You don’t have to wake up at the crack of dawn to fly out of Pearson at 8 am. Instead, I was able to book a car to pick me up at 9 for an 11 am flight. When I got to the airstrip, I checked in and was escorted to the plane by my Client’s assistant who greeted me with a cashmere throw (in case the AC was too high) and a pair of slippers to change into. On the plane, I was greeted by the pilot and the flight crew and told that we would depart as soon as my Client arrived. I slipped out of my heels and settled in for our vacation.

I’m so happy that I dressed professionally for the flight, since my Client was wearing a three piece suit when he arrived. With a shy smile, he greeted me with a kiss on the cheek and asked if I was comfortable. Always the gentleman, he excused himself to greet the pilot and review the flight plan, and when he came back, I saw that he had already removed his jacket and tie.

Once we were in the air and able to move throughout the cabin, the crew served us a late breakfast. I mean, why have plane food when you can have takeout from a 5-star restaurant on the ground? We toasted to our new adventure and I couldn’t help myself, a happy little purr escaped as I snuggled into the cashmere throw.

“First time?”

“You can tell?” I could feel myself blushing with inexperience; it’s not often that I’m the inexperienced one on a date.

“Don’t get me wrong, you are obviously used to the better things. But I could tell from the way you were paying attention to the flight prep. Don’t worry, by your third trip this will all become white noise.”

“…by your third trip.”

I took a sip of my mimosa, enjoying the sensation of the bubbles evaporating on my lips.

I smiled and said (half) jokingly, “oh I’m not sure about that. I doubt other flights will be as special as this one. After all, one never forgets their first.”

He matched my smile and said, “we can revisit this conversation on that third trip.’

I wasn’t sure if it was the magically refreshed drink, or the promise hidden in that statement, but a warm buzz took over as I found myself reaching a new altitude for living. It was kind of hard to keep him entertained for the rest of the flight, as he was still technically connected to the office via wifi. When the pilot announced we were about to make our descent, I looked over at him and asked if he could make me another promise.

“I might be able to. What would it be?”

“When we land? Work stops. I have other plans for this trip, and your work doesn’t fit in with those plans.”

His smile told me that he would definitely be able to keep that promise.

From the moment we landed, I got to see a different side of my Client that I was very happy to see. It turned out that our trip was his first real vacation in nearly 15 years. Real in the sense that he completely disconnected from the office, and gave himself up to all the indulgences the island had to offer, which was four days and three nights of non-stop fun and entertainment. When it was time to pack up and go home I could already feel the post vacation blues set in. Pulling up to the plane, I could see that he was also making the transition back to work life. He was tanned and relaxed, but ready to dive right back into long days and lonely nights.

When we got back home and we had to part ways, I told him how much his vacation suited him and told him he should not wait another 15 years to take another one. That shy smile appeared and he said, “how about another one in 15 days?”


I have to sign off on this story now; we’re getting ready to take off.

I love it when a man keeps his promises.

Photo by Pexels

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