While on vacation in Southern Portugal, I had an experience that I believe to be very unnerving. I had someone who made my family feel uneasy.

The saga involved location confusion, some odd message exchanges in the Uber app, a request to connect outside the app, and then after the ride was canceled, an awkward appearance from the driver, with an offer.

I spent the day trying to figure out what the intentions were, and I wanted to ask our large and knowledgeable community for their opinion or insight.

The Play By Play

My wife, two year old and I were staying at a gated resort in Southern Portugal with some of our best friends for the last few days.

The easiest way to move around was to take two Ubers. I hailed a ride with no Black service in the area and was connected to someone ahead of my friend. All went well.

My friend's ride showed up before mine, and my driver started texting me to say he was on location. This was a walled and gated resort with only one accessible entrance.

We left the gate and went to the public road to wait. There were no questions about the ride pick up spot on rides before and after. Everyone else got there at least 10 times.

It Gets Weird

The guy insisted he was there. I kept saying I didn't see him, but I offered up as much helpful information as I could, such as the resort name, the specific street and cross street.

He wanted me to call him on his mobile phone. It would have been easy for him to call me via the app, but he insisted on using his personal phone.

I canceled the ride because I was frustrated and not into that out of app route. I got a new crack at someone who could find the place which everyone else found without issue after he got something.

I wasn't going to start down that route because I didn't want to lose my protections when I went outside of the platform. I like the safety features that they have added. I wanted them to work for me.

I hailed a new ride on the app and the driver was 5 minutes away. A car matching the description of the ride I just canceled shows up.

I am from New York and travel frequently. I lived in some rough neighborhoods in my 20's, so I would like to think my radar is good. My perception as the car approached was that the driver looked at my wife and two year old and that he had a variety of thoughts in his head.

He rolled his window down and asked if he had canceled. I apologized for the hassle. I was charged a cancellation fee and hope it helps settle your time.

Here’s where it gets just flat out intimidating and bizarre…

The driver takes another up and down of the three of us. I said something along the lines of "That's very kind, we're all good and have a great day, another car is coming, or something like that." I thought it would end there.

No harm, no foul. I wasted 10 minutes because he got paid.

The car went into reverse after I heard it shift into gear. In a small town, this is a pretty desolate road. It is not in a city center or a bustling avenue. A quiet residential street leads to a mediocre resort.

The driver reversed out of sight of the guard booth and put the car in park. I thought he was changing a shirt or getting something from his car, but he kept watching me. He asked if a car was coming.

I said thanks, but he remained there. The guy kept watching us as we waited for our ride, but we were a few feet closer to the guard entrance.

I was trying to avoid eye contact and was hoping the new ride would show up early. He asked us about a ride, but then looked at us in a strange way and drove off.

Our new ride came shortly thereafter and we had an entirely uneventful evening, but the incident was all I could think about for the rest of the evening.

Intimidation Or Kindness?

I am definitely a glass half full person. The Sing 2 side of me wants to believe that he was just trying to be helpful and help if needed. I feel bad about the apprehension if that was the case.

I don't usually feel that way, but everything about the incident felt frightening and intimidating. There are a variety of reasons for canceling on both ends of the spectrum. That is the end of it.

This was the first time I had someone drive to find me and ask me about a cancellation. It might be off-putting to some. The desire to connect outside of the app didn't make me feel any better.

It made me uneasy that someone would want to take things offline, particularly now that I knew where I was staying.

After declining the drivers offer of a ride, parking, and sitting on an empty street next to us, it felt completely weird. If it was well intentioned, I read it wrong, but it didn't feel that way.

What I’d Like To Know

I'm curious to learn if there are protocols or no-no's for drivers for certain situations. If a rider cancels, is there something that says not to approach the customer or try to find them?

I was charged a fee since the guy spent 10 minutes telling me where I was and then I canceled.

The effort to reach me was well intentioned and hoped to assist, but he seemed to get there quickly once the cancellation happened, and not so much in the 10 minutes before.

I don't want to cause any drama to the person, but I think this was odd and wouldn't be in the best interest of the company. I may change my mind if there are clear rules or protocols.

If this had been a residential street and there had not been a guard booth and gated complex, I would have called the police. I got a vibe from the person that I rarely get, and it felt like intimidation.

Was this guy trying to be nice or not?

Can saying no lead to better rates? I am the first to admit that I am lazy. I am tempted to use the app to get home, rather than take the subway and walk 15 minutes. Every once.

In opinion.

These are all first world problems. I understand that my phone couldn't hail a car immediately when I wanted it. It is not the end of the world, but it is a travel business in a competitive, customer forward landscape.

Travel experience reviews.

I became an evangelist when the ride-sharing company came out. I told people how easy it was and I downloaded the promo code onto my parents phones to get them closer to the exciting new travel action. It was a genuine game change.

Travel experience reviews.