My Life As the Family's Plus-one
- stephaniewilson
- May 1, 2023
- 4 min read

I’m sure the reason I’m the date of choice among my siblings is that I have otherworldly entertainment value. Although, it’s possible the fact that one sister didn’t have a boyfriend and the other sister’s husband was overbooked might have factored into each of them asking me to accompany them on their respective work award trips.
The first trip took place in the 1990s, the second trip was just last week. Both are keepsakes in my ever-flagging memory.
I’m the oldest of four kids — two sisters, one brother. The older of my sisters asked me back in the 90s if I’d be her date on a cruise she’d won for her performance at work. They’d fly us to Miami, and we’d embark on a multiday cruise to the Bahamas. I said yes in a heartbeat. It was a span of Caribbean breeze, clear water swims, lazing, laughing, and one short stint at the ship’s casino.
Our dad had given each of us twenty bucks to bet at the casino. We walked in, placed the bill down on a roulette table, lost, then walked out. Gambling wasn’t our thing.
But pina coladas were. We were hardly the party-hardy types, but opting to have someone wait on you hand and foot while you lounge on the deck of a ship was a no-brainer. I haven’t done it since.
There are sparkles of the trip still floating in my mind. We did skeet shooting off the ship’s deck. We languished on a small island. We snooped around the port to take in the tourist scene.
The top memory for me of all the trip’s flashy things was a short moment in the small cabin we shared. It was at night while we were winding down for the day, and my sister started to tell a story about a college assignment years before. She’d been tasked with developing a presentation and delivering it to the class. The students were given weeks to work on it.
My sister never quite got around to starting the project until the night before. She panicked and scanned her mind for something she could throw together. She decided she’d re-pot a plant because of a recent summer stint at a garden center. She’d give a live demonstration while explaining all the intricacies of re-potting, of which there are few. The story of the mishaps of how the presentation transpired is still one of the funniest things I’ve ever heard. We laughed til we cried.
Do I remember most of that trip? No. But I haven’t let go of that moment of shared laughter.
Flash forward to last week. This time my youngest sister asked me to accompany her to Orlando, Florida for a few days of all-expense-paid extravagance. It was deluxe, with a mix of free time and daily functions we were expected to attend.
For this trip, we had an itinerary with a dress code for each event. Our suitcases were jam-packed. I was beyond impressed with how many shoes my sister was able to squeeze into a smallish suitcase. Just so you know, we’re capable of more than we realize.
The affair was generous and thoughtful. The C-suite appeared in shifts at each event. I learned the award was very competitive. I told my sister multiple times how proud I was of her.
We had the choice of an offsite excursion from a long list of rather cool things to do. My sister and I opted to zipline over alligators at a big reptile park. We ogled, jaw agape, at the mounds and mounds of alligators everywhere. We freaked out on the zipline until lightning shut it all down enabling us to shop for alligator swag.
Later, a visually stunning dining room at the hotel complex hosted the big group, and there was dancing into the night. This was followed by a group charity event where we assembled children’s bicycles and painted duffle bags for a non-profit that helps foster children. There was so much to take in, lots of activity, and I learned some things.
Yet, the one thing I know I’ll take with me long into the future is that first afternoon when my sister and I arrived. We put our luggage into our hotel room, then wandered around the property, exploring. At one point, we came across a hammock stretched between two palm trees, and a hanging chair next to it.
“You want to sit for a while and chat?” my sister asked.
“Sure.”
We rocked gently back and forth on our seats and talked. My sister shared what had been on her mind lately. I listened and chimed in, too. The palm fronds fluttered in the breeze. It was beautiful to be calm and easy, swaying in the warm air, held in the intimacy of a sister friendship. It was so precious to me.
What have I noticed? The same thing I’m always noticing about life. I’ve had fascinating experiences through the years, and yet, the pieces most deeply embedded in my memory are the people I shared them with — the heartfelt, vulnerable, and joyful moments with others.
The longevity studies keep telling us this, I know, but it’s firsthand knowledge that gives the gut understanding of how important our connections are. I’m the luckiest girl in the world to be the family’s plus-one. Where to next, ladies?
Hope you're well, friends.





Thank you for beautifully capturing our trip. Love you sis!