I have been traveling a lot for work and, since we only have one car, that often means taking a taxi back and forth to the airport.

Hypothetically, taking a taxi isn’t too bad. I call ahead and schedule a taxi to pick me up at my desired time. Everything is nice and automated and they send you a text when they arrive. There’s only one route to the airport. I’ve done it enough times that I know approximately how much it’s going to cost. Easy peasy. However, I’m growing to dislike it so much it’s starting to border on phobia.

There are two types of taxi drivers: the ones that want to make conversation the entire way, and the ones that talk endlessly on their bluetooth headsets in their native language. I VASTLY prefer the latter. Keep in mind these taxi rides are either to the airport at about 4 a.m. or home in rush hour Chicago traffic after a long day of travel. I really don’t feel like debating politics with a cab driver in either of those circumstances. I really don’t. I’d much rather zone out to the soothing sounds of your incomprehensible conversation.

Actually, there is a third kind. Often a driver will think it’s a good idea to harangue me the entire time, in an effort to increase his tip. Mostly this is about how he had to sit out front for so long (despite the fact that I was watching out the window and came out 10 minutes before my scheduled pickup time) and how that costs him money and how really it’s kind of my fault he’s driving in this awful traffic all the way to the airport of all places, so maybe I should just do the right thing when it comes to tip time, you-know-what-I’m-saying? And by the way, did he mention how the city is screwing him over? And the tax man? And gas prices?

There is nothing that upsets me more than feeling like someone is trying to artificially tug at my heartstrings. It certainly doesn’t put me in a tipping mood. How does this work on anybody??

Even in the best of circumstances, tipping people always causes me an unreasonable amount of anxiety. But this is especially true when it’s in some sort of hurried situation (such as trying to pay while hopping out of a taxi at a busy intersection or airport). This is my fault, not theirs, but there it is. Once I get about 15 minutes out from my destination, I start sweating and endlessly calculating all the possible scenarios in my head. “Okay, so I will just give him Y and tell him to keep the change. Is that enough? It’s probably good right? Wait, did I calculate that right? Let me recalculate. Yeah, I think that’s right. Wait, the meter just rolled over to another dollar. Is that still a good tip or should I bump it up to Z?”

That’s my neurosis, and if that were the only problem, I could handle that. However, around the same time I have to start worrying, “How is this guy going to try and screw me over?” and preparing myself to be belligerent (I have to work myself up, just in case, but that’s okay because it’s almost always necessary).

In roughly 8 of my taxi trips, the credit card machine “mysteriously stopped working” about 5 minutes away from the airport. “Oh, sorry sir, you’ll have to pay cash.” To which I respond, “Well, you’ll have to call it into dispatch or else you’re not going to get paid.” Guess what? The credit card machine mysteriously starts working again! EVERY. SINGLE. TIME. I understand they’d rather be paid in cash, but I’m taking two cab rides that are between $65 and $70 each. I’m not carrying $140 in cash, just for the taxi ride. I’m just not.

Since my too-bad-so-sad attitude seemed to be working fairly well, they have recently come up with a new scam. On the last two cab rides I’ve taken, after they claim the credit card machine is broken, they pull out their Square credit card reader for their iPhone. They swipe your card on their iPhone and then you get a charge from “Frank’s Cab Service” rather than the taxi company (and also, I assume, they get to keep your credit card number).

This makes me *extremely uncomfortable*, but I haven’t figured out how to handle this yet. For some reason I feel uncomfortable just flat out refusing, but I don’t know why. One of the times I got away with it by saying I needed the receipt for work, but the other time the guy promised me the receipt would be emailed to me (and it was). So I actually did pay by Square that time, and it seems to have worked out for me. I assume, however, that my luck would most likely not continue to hold on that one.

Long story short: cab drivers are some shady characters and I have to put up with their b.s. on top of paying them a ridiculous amount of money for the privilege of going through airport security.

Not every taxi ride is trouble, but because 85% of my experiences are bad, I spend most of my time fretting and anxious. Time after time I have had to deal with it, until it just becomes the rule, not the exception. The fact that I’ve had so many bad experiences just proves that it’s not just my bad luck: the vast majority of cabbies are just a cut above your average panhandler.

I like the idea of being able to catch a cab when you need it, but the reality is a far cry from the ideal.