Yesterday, while on vacation in Southern Portugal, I had what I believe to be a very creepy Uber experience. That, or I had someone who was very well intentioned, but 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 cancelled, an awkward and lingering appearance from the driver, with an offer.

I spent the day trying to mentally unpack what the perception or intentions might have been, and I couldn’t help but want to query our large and knowledgeable community for 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 size of the group meant taking two Ubers was generally the easiest way to move around. Yesterday afternoon, I hailed a “comfort” ride, with no Uber Black service in the area and was quickly connected to someone ahead of my friend. All uneventful.

Until, of course, my friend’s ride showed up before mine, and my Uber driver started messaging me to say he was on location. For the sake of clarity, this was a walled and gated resort with only one accessible entrance.

We went out of the gate and on to the public road to wait, to save time and formality. On rides before and after, there was never any issue or question about the ride pick up spot. Everyone else got there 10/10 times.

It Gets Weird

This guy kept insisting he was there. I kept saying I did not see him and kept offering up as much helpful information, such as the resort name, the specific street and cross street and so forth as I possibly could.

After an odd back and forth, he wanted me to call him on his personal mobile. It would’ve been easy for him to call me via the app, or vice versa, but he offered up his personal phone and insisted.

Frustrated and not into that out of app route, I cancelled the ride, with a cancellation charge. Not ideal, but whatever, he got something and I got a new crack at someone who could find the place which everyone else found without issue.

Riders lose all protections once they go outside of the platform and I wasn’t about to start down that route. I like the safety features Uber has added. I wanted them to work for me.

Fast forward 5 minutes, I’ve hailed a new ride on the Uber app and a driver is like 5 minutes away. Suddenly, a car matching the exact description of the ride I’d just cancelled about 5 minutes ago shows up.

I’m from New York, travel often and have seen some things. I also lived in some rough neighborhoods in my 20’s, so I’d like to think my radar is decent. My perception as the car approached was that the driver sized me up, noticed my wife and two year old and a variety of thoughts went through his head.

He rolled his window down and said “did you cancel?”. I said “Yes, I did, I’m sorry for the inconvenience. I got 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, and says “I can take you”. 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. He seemed to acknowledge and I figured it would end there.

No harm, no foul. He got paid, I just wasted 10 minutes, standard.

I heard the car shift into gear, but the car went into reverse, not drive. Mind you, this is a pretty desolate road in a small town. It’s not in a city center or bustling avenue, or near food. It’s a quiet residential street leading to a highly mediocre resort.

The driver reversed about 5 feet, out of sight of the guard booth we were basically next to, and put the car in park, engine running. At first I assumed he was perhaps changing a shirt or getting something from his car, but he kind of just kept watching me. He then asked again if a car was coming.

I again confirmed one was coming and said thanks anyway, but he remained there. We drifted a few feet closer to the guard entrance and just waited for our ride, but the guy kept watching.

At this point I was doing my best to avoid eye contact and was really hoping the new ride would turn up early. About 3 minutes later, he made one more pass at asking us about a ride, while looking at us in a peculiar way and eventually started to drive off.

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

Intimidation Or Kindness?

I’m definitely a glass half full person. The Sing 2, “kids movie” side of me wants to believe he was just trying to be helpful and be around to assist if needed. If that was the case, I feel a bit bad about the apprehension.

But everything about the incident felt unnerving and intimidating and I don’t usually feel either of those things. Cancelling happens on both ends of the Uber spectrum for a variety of reasons. Typically, that’s the end of it.

This was the first time I’ve had someone actually drive to find me and ask me about a cancellation. That in itself might be off-putting to some. I could get over that, but the desire to connect outside of the app didn’t make me feel anymore at ease.

In fact, it made me feel really uneasy that someone wanted to take things offline in this way, particularly now knowing where I was staying.

After declining the drivers proposition of an off the Uber books ride, parking and just sitting on an empty street right next to us just felt entirely creepy. Again, if it was well intentioned, I read it wrong, but it did not feel that way.

What I’d Like To Know

I think the main thing I’m really curious to learn here, is if there are protocols or no-no’s for Uber drivers for certain situations. Like, if a rider cancels, is there something that says do not approach the customer or try to seek them out.

Obviously I got charged a fee, since the guy spent 10 minutes telling me he was where I was and then I cancelled, so he got something, but yeah — I dunno.

I’d like to believe the effort to reach me was well intentioned and hoping 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 undue drama to the person, but I also feel like this was odd and wouldn’t be in Uber’s best interest. If there are in fact clear rules or protocols, I may change my mind, based on what’s learned.

All I know, is that had this been a solely residential street, and had there not been a guard booth and a gated complex feet from where I was standing, I probably would have called the police. It felt like intimidation and I got a vibe from the person that I rarely get.

So, was this guy probably trying to be nice, or is this very creepy?

Gilbert Ott

Gilbert Ott is an ever curious traveler and one of the world's leading travel experts. His adventures take him all over the globe, often spanning over 200,000 miles a year and his travel exploits are regularly...

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16 Comments

  1. Flag it with Uber support – this guy was trying to play you to have you cancel, then take an-off platform ride to get a higher fare. There’s too many drivers on the platform that know the ‘I’m here but can’t see you’ trick to get you to cancel.

  2. Yeah, I’d say he was just trying to be nice/helpful. Small town in Portugal, probably wanted to make sure you weren’t stranded if the next Uber didn’t come. I wouldn’t think much of it or let it bother me too much. Uber has instituted a lot of new safety features which seem pretty helpful on the surface.

  3. I would have been weirded out by that experience too. You made the right choice and you may have dodged a bullet by avoiding what would have basically been an unlicensed cab. I wouldn’t jump to the conclusion that there was some malicious intent, though and personally I wouldn’t dwell on it or bother following up with Uber.

  4. Why are you happy to pay this cancellation charge? He clearly was not at the agreed pickup location, wasting you 10 minutes and causing trouble because your friends had already left and were bow left waiting. In this instance it’s ok to give the driver a few minutes to find the right place but if he doesn’t and insists he is on location, why should you have to pay him for his failure to pick you up somewhere?

    It’s like ordering a taxi, the taxi never shows so you just walk but still pay the taxi…

    1. Honest answer? Because the amount was entirely insignificant to my life, but may have helped the person get through the day. Say what you want about it, but I’m a let it be person, and if it made any difference in their take home, or their stress levels, it’s more important for them to have that than for me to have a few extra euros.

  5. I 2nd Dave I would dispute the cancellation. It’s not my job to pay people for no reason. I do charity by other means directly to those in need not by letting greasy people scam me.

  6. You’re in low season in a country with an average salary of ~ 1,300 euro/month, highly dependant on tourism and struggling after covid. My guess is he just wanted to take you and earn the full fare.

  7. My thought is that he may have been desperate for business. Lying to say he was there, in the hopes that you’ll wait, then hanging around hoping you don’t wait for your other ride. Either way, unprofessional. I’m not ruling out creepy either and I’d report him to start/enhance a paper trail. Uber has safety processes in place for a reason, and he needs to follow them.

  8. I can’t claim to be intimately familiar with small-town-Portugal social mores, but if I’d experienced that chain of events in any of the myriad of destinations I’ve reached across the globe over the last 25 years, there would have been some serious alarm bells going off. Absolutely zero question.

    I would also report the incident to Uber.

    Out of principle, I’d also appeal the cancellation fee, especially if you have text message records of your exchange with the driver which illustrate that he was not where he needed to be.

  9. Nooope. Definitely creepy. I’m a woman and I often travel alone so I also have a pretty good radar and that would have weirded me the hell out. I mean, it’s possibly unintentionally creepy but there are too many weird things about this story for me to dismiss it as benign. Glad nothing bad happened.

  10. Whatever your gut tells you is always right, unless proven to the contrary. This is easy to say, but hard to act out due to social conventions. However, life has taught me again and again that this is a vital rule.

  11. Unfortunately, this is a game with Uber drivers. We’ve seen it in Thailand in the past and most recently in Turkey. The driver calls saying they can’t find you, or they are at the location, or some other fake reason to get you on the phone. They want to know your destination – then they either demand a price that isn’t what Uber says it should be (Thailand), cancel the ride, tell you to cancel, or try to get you to go off the Uber app. All total BS. I used to prefer Uber to taxis because generally, they were more honest. Not anymore.
    While it may or not have been creepy – it certainly wasn’t with innocent intent. You were at a resort – so you wouldn’t have been stranded. He would know other drivers would be available – he was just hoping you’d give in and give him the fare.

  12. The driver is unquestionably weird. He was at the wrong location. I am glad you’re fine! Please be safe!

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