My name is Alyssa, I’m 25, and I live in Portland, Oregon. I’ve been using dating apps on and off for the past year, and honestly I’ve had my fair share of weird dates.
But this one might be the strangest so far.
About two weeks ago I matched with a guy named Ethan (28). He seemed normal enough. We talked for a few days, mostly about work, favorite food spots in Portland, and hiking trails around the city.
Nothing unusual.
After about a week of chatting he suggested we grab coffee at a small café downtown. I agreed because coffee dates feel low-pressure and easy. If the vibe is bad, you can leave pretty quickly.
The day of the date I showed up about five minutes early. The café was busy but cozy, the typical Portland vibe — lots of plants, people typing on laptops, indie music playing quietly.
I texted Ethan that I had arrived.
A couple minutes later he walked in.
But he wasn’t alone.
There was a woman walking right behind him who looked to be in her late 50s. At first I assumed maybe she was just another customer walking in at the same time.
Then Ethan waved at me.
And the woman waved too.
My brain was trying to figure out what was happening as they both walked over to the table.
Ethan smiled and said, “Hey! This is my mom, Linda.”
I honestly thought he was joking.
I laughed awkwardly and waited for him to say he was kidding.
He wasn’t.
His mom sat down with us like this was completely normal.
At this point I’m already confused, but it somehow got even stranger.
Linda immediately started asking questions.
Not casual small-talk questions either.
More like interview questions.
She asked where I went to college, what my career goals were, whether I wanted children someday, and what my “long-term financial mindset” looked like.
I wish I was exaggerating.
At one point she literally asked, “How do you usually handle conflict in relationships?”
Meanwhile Ethan just sat there sipping his coffee like this was totally normal behavior.
I tried to laugh it off at first, but after about ten minutes it really did feel like I was in a job interview.
Linda even took notes on her phone at one point.
Finally I asked Ethan, “So… is this something you usually do on first dates?”
He shrugged and said, “My mom just likes to make sure I’m meeting the right kind of people.”
That was the moment I mentally checked out.
I finished my coffee as quickly as possible while answering the least personal versions of her questions.
Then I told them I had another commitment and needed to leave.
Linda said it was “very nice meeting me” and that she appreciated my honesty.
Ethan texted me later asking if I wanted to go on a second date.
I didn’t even know how to respond.
Because apparently dating in Portland now comes with a parental screening process.
So yeah.
Safe to say that was my first and last date with Ethan.