Sixteen Going on Twenty
Updated: 1 day ago
My teenage niece and I were in Hawaii with family, staying at the Prince Waikiki in Honolulu. It was one of those beautiful vacation days when you really do feel like you're in paradise.
We were at the pool, doing what aunts and their young nieces do on vacation in Hawaii. Looking for cute boys. (Read about one of our other vacations here.)
She spotted one.
He had brown hair with big, loose curls that were a little on the long side, a nice tan, and boyish good looks. We giggled and watched him and his mom get into the hot tub in front of us.
Unfortunately, it was packed with little kids, so they didn't stay long.
A little while later, we saw him in the infinity pool, looking out over the marina. The sun was starting to go down.
My niece joked about going over there.
“Let's go,” I said.
She looked at me, shocked that I actually meant it, but followed me as I walked over and got in the pool near him.
I started talking to her about how crowded the hot tub had been and joked that maybe they should limit how long people could stay when it was crowded. Maybe there should be an adults-only time.
He turned around. “I agree,” he said. “There should definitely be an adults-only time.”
“But you don't look like you're an adult yet,” I teased.
He laughed and said he looked younger than he was.
“How old do you think he is?” I asked my niece.
“Seventeen?”
“Higher,” he said.
“Eighteen?”
“Higher.”
“Nineteen?”
“Higher.”
“Twenty?”
“Twenty.”
Then my niece asked him to guess our ages. He looked at her.
“Eighteen,” he said.
I had a feeling he was hoping she was.
She wasn't. She was sixteen.
I told him my son was twenty-one and had just finished college and asked if he was in school. That's when he started telling us about himself.
He had a high GPA but didn't want to go to college. He didn't like school and said he didn't really relate to the kids in high school. He was interested in law and talked about a lawsuit his parents were involved in over a business dispute. He cared about fairness.
He was also interested in psychology, like his younger sister, who was about to start studying psychology at the University of Hawaii.
He wanted to understand people.
My niece was quiet at first, so I carried most of the conversation, trying to give her openings when I could. Then she started jumping in.
She told him about her AP psychology teacher, who she thought was very strange. He laughed and started telling us about his strange psychology teacher in high school.
The conversation just kept going.
I watched my niece get more comfortable.
Eventually I started to get cold.
“I think I'm going to try the hot tub again,” I said.
I left them talking.
When I stopped back a while later, I had her phone with me. I had previously mentioned that I wasn't very good at taking pictures for her Instagram, and he had said he takes pictures for his sister all the time.
“Will you take some pictures of her?”
He did.
They were both in the infinity pool, looking out over the marina and the sunset, and I snuck a picture of them from behind.

A couple sitting nearby had also asked him to take their picture. After he left, they told my niece what a nice couple they thought the two of them made.
He eventually had to go meet his family for dinner at Earl's. He explained that they had reservations but stayed as long as he could.
And that was it.
Or at least we thought it was.
The next day, my niece told me something else they'd talked about after I left. He had asked if she drank.
She told him her parents had let her try alcohol, but she didn't like it. Neither did he. He said his parents had done the same with him and that he thought kids were often tempted by things they're kept from.
I thought that was an interesting question for him to ask her.
A couple of days later, my niece and I were leaving the pool and went to the elevator, a little sad that we hadn't seen him there.
The doors opened.
There he was.
They said hi, then they both froze. The elevator was crowded, and suddenly neither of them seemed to know what to say. My niece looked paralyzed with shyness. He looked almost guilty, as if he'd been caught doing something he wasn't quite sure he should be doing.
I looked at both of them, amused.
“What are you up to tonight?”
He rambled a bit awkwardly about heading out for a casual dinner with his family. Three floors later, the elevator doors opened and we said goodbye.
Later, we found ourselves in the hotel lobby around dinnertime, half hoping to see him.
And we saw him.
He was wearing a white button-down shirt and khaki shorts.
So cute.
By then, this had become a family sport.
The next day my cousin was in an elevator with her baby when she spotted him and his sister. She took a stealth picture of the baby in the foreground and sent it to us.
“Possible Cole sighting?”
It was him.
We were on the tenth floor. He was on the eighth.
What were the chances in a hotel with two buildings and 500 rooms?
My niece and I were still talking about him after we left Hawaii.
She was disappointed he hadn't asked for her number.
I told her, “If he had asked for your number, you probably wouldn't have liked him as much.”
She thought about that.
Because the thing she liked most about him was how easy it had been to talk to him.
There hadn't been any of that awkward teenage performance where everyone is trying to impress everyone else. He didn't make her feel pressured to flirt back. He just talked to her.
And he knew she was sixteen.
He was twenty.
So he didn't ask for her number.
I think that was probably the most romantic thing he could have done.
A note on the title: Inspired by “Sixteen Going on Seventeen” from The Sound of Music.
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