That Girl: Are poolside pickups appropriate?

That Girl: Poolside Pickup, Twin Cities Agenda

I haven’t been dating. I’m in between jobs at the moment, so my energy and confidence are not as high as they should be. Life has proven to be a bit of a challenge lately, so my dating life has been, well, rather stale.


I hadn’t even been asked on a date in a while, up until a few days ago: It was a weekday, and I knew I needed a hefty dose of vitamin D. I am blessed with access to a pool in the backyard of my condo, so I went to find some sun and solace.

It’s always busy at the pool on weekends. Understandably so, given the weather. Residents are allowed to bring visitors to the pool as well, so it’s usually stays packed all summer long. And, being an extreme introvert, I typically avoid it at all costs for this reason.

But, it was a Tuesday afternoon and I found myself enjoying the pool with my latest summer read in hand. Solo. It was total bliss.

Hair in a bird’s nest bun on top of my head, my face without makeup, and allowing myself to be free from any care at a pool that was absent of any visitors. I soaked it all up. 

Pool pickups, Twin Cities Agenda

The sun gets hot after a while and the pool is a refreshing release. So I find myself cooling off in the pool after a couple chapters in.

Suddenly I hear, “Hello, in there. How’s the water?” from behind me. I had been so lost in the blissful quiet of the pool, I hadn’t noticed the presence of a new visitor.

I turn around to find a man sitting obscurely at one of the poolside tables facing the water. While I don’t love small talk, and I was looking to enjoy my solo time, I am good at bullshit-and-banter. So, I decided to be friendly and chat a bit with a stranger, without thinking much of it.

Before long, however, he was asking for my number and telling me how respectful he was for a man.

Ummmmm… “What. Is. Happening?” I thought. 

He was probably a decade-and-a-half older than me, and the request came as if from nowhere. I wasn’t sure what to think: It’s either highly coincidental and super cute… or totally creepy. I cannot decide.

In a strangely short amount of time, I found out this man “owns several homes,” had recently gotten a divorce, and has partial custody of a teenage son. All the while, mind you, I’m still treading water by myself in the shallow end.

A few minutes passed and, thankfully, more people arrived at the pool. It was the end of the workday, solo pool life had officially been blown to shreds.

But the distraction of the new-comers was welcome, and I find my way back to my lounge chair and summer read.

I thought all was good to go – that I was in the clear – until he, and his son, come to say goodbye and he proceeds to ask for my number and a date.

Confused, and caught off guard I said, “If it is meant to be, I will see you again.”

Poolside pickups, Twin Cities Agenda

I haven’t been to the pool since.

So my question, friends, is this: Was this encounter something I could consider flattering? Or totally creepy?

I’ve done the dating-someone-in-your-building thing, in the past, and it didn’t go well. Am I overthinking this? Or, is it a good idea to stay away from the stranger that appeared randomly during my solo swim?

And, as the questions remains, how much does (or should) his age matter?

Read next: That Girl: Dating younger guys vs. older guys