[If you haven't read my blog in a while, I hope you'll read this post because in addition to a general dating etiquette reminder I shouldn't have to make, the last couple of paragraphs also contain an important safety PSA that I really shouldn't have to make.]
I ended up postponing our date after I got in from a red-eye and had been yelled at by one too many passengers that day. I wasn't feeling much like being around other human beings that day, and I figured I wouldn't be giving Mr. Uber a fair chance if I went out with him in this mood. Besides that, he'd mentioned recently having had a nasty sore throat, and I figured he'd be relieved to get a little extra recovery time. (That, and I won't pretend my desire not to get sick myself wasn't a contributing factor. It definitely was.)
So Thursday night at last we met up. To Entrepreneur's credit, he chose a good location. I happen to be a big fan of Antique Taco in Wicker Park, and if you haven't been, you should definitely give it a shot. (Pro-Tip: Try the rosemary margarita. And if you're on a first date, I can say as someone of moderate-to-slightly-above-average alcohol tolerance, I drank one of these and didn't feel anything, so they're not dangerously potent when paired with food.)
Also to his credit, Mr. Entrepreneur is a good conversationalist, and that is a great skill. He has a tendency to abuse the phrases "Nailed it," and "Fair enough," a little too much, but we'll chalk that up to nerves around a perfect stranger. Otherwise, he can keep a conversation going and more or less interesting, which, sadly, is a skill not everyone has. So props to him. "Nailed it."
Sadly, that's about where the good stuff ended. He was late for a 7:00 date, and didn't tell me until 3 minutes beforehand, meaning I had just arrived. So I got to sit around and wait on him for about 25 minutes. Thank God I bring a book literally everywhere I go. He was very apologetic about being so late, but never really gave a satisfactory reason why he was so late, rather he made the mistake of saying it was for something "Stupid." Which I realize he meant to sound like whatever happened was less important than this and he was sorry about it, but it kind of made me feel like even something stupid was more important than being here on time.
I'll bet you're wondering why I'm calling him Mr. Entrepreneur. Well, when I pressed him to tell me about whatever "stupid" thing made him late (Not in a mean way, I promise. In a pleasant, conversation-making, forgiving way.) he explained he was making "some business deals."
He spent much of the evening telling me about his free-lance work as an audio-editor and the numerous small businesses he is trying to start, and the clients he has attained through odd interactions, and the fact that he is trying to capitalize on PokemonGo's popularity and make money off of creating meet-ups. All relatively interesting stories told in an intentionally humble-brag manner and almost definitely designed to impress me. Unfortunately for him, they had the opposite effect. What I gleaned from him is that he has no solid, focused career plan, and is pretty much flopping around anyway the wind blows him. Which is completely fine! I realize I probably sound pretty judgmental right now, but understand that I'm not looking down on him for this. I actually think the guy has a certain amount of business savvy to support himself off of what he's doing work-wise. That said, I find it totally unappealing in a potential partner. I've crossed the invisible boundary from my early 20s to my late 20s, and what was once perfectly acceptable now makes me cringe. I'm looking for stability and security in a relationship with a man, as well as focused ambition. Let's face it. I'm looking for a guy with a 5-year plan that I can comfortably introduce to my grandfather and not have to worry about what questions Grandpa might put to him.
Just not what I'm looking for. Sorry, Mr. Entrepreneur! Better luck with another lady.
If you still think I'm being too harsh or too picky, then I'll throw in the fact that he broke the cardinal rule: He asked me out. He chose the restaurant. And he not only didn't pay for my meal, I don't think it even occurred to him to offer to pay for my meal. Which, quite frankly? Screw you, Mr. Entrepreneur, I have had some serious unplanned expenses lately and my bank account is extremely tight. If you didn't want to pay, you should have asked me where I wanted to go, and I would gladly have suggested something free to do. As a matter of fact, Thursday is free-entry day at the Art Institute of Chicago. I would much rather have done that than throw away another $17 of money I don't happen to have right now.
This actually leads me to a theory I'm forming. Remember Mr. Bumble and the coffee date he didn't pay for? (Which I was far more forgiving about because a coffee is only around $3.) Well, I'm thinking if a guy takes you somewhere where you have to wait in line to order or purchase a ticket, assume that you'll be paying for it. I distinctly remember a guy taking me to the movies when I was 17 and awkwardly pausing while waiting for me to purchase my ticket and then still more awkwardly stepping forward when I hesitated and saying "Uh, 2 for Indiana Jones? I mean 1. I mean 2!" (The horror. Couldn't make eye contact with him the rest of the night.)
The more I write about this the more irritable I find it is making me. I get it, people, dating can get expensive. Going out at all can be expensive. But the ettiquette is that whoever does the asking needs to do the paying, shy of extraordinary circumstances. As the invitee in the situation, I am a firm believer in offering to split because it is good manners. That said, the ask-er should insist, be they man or woman, hetero-, homo-, bi-, or pan-sexual or whatever else they've got labels for these days.
Therefore dear ask-ers? If you can't afford to pay for a meal, go for a drink or a coffee. If you can't afford that, I would like to take this opportunity to remind you there are a 1001 free things to do in a metropolitan city like Chicago that make for a great first date.
Pfft. And he looked so surprised when I turned down his offer for a ride home in favor of taking the train.
Which reminds me: To the men of the world, for crying out loud, please understand that dating is dangerous for women. I don't care that you know someone in my building. The fact that you know which building I live in already makes me considerably nervous. DO NOT TRY TO FIND OUT WHICH APARTMENT I AM IN. DO NOT ASK A WOMAN WHERE SHE LIVES ON A FIRST DATE, ESPECIALLY AT THE BEGINNING OF A FIRST DATE. I don't care what story you have that gives you a "good reason" for asking. I don't care that you probably have no intention of kidnapping, raping, or stalking me. What you need to understand is that before I left to meet you this evening, I gave two friends your full name, the location we were meeting, and a code-phrase that meant "Call the police." Because the odds that you are planning to kidnap, rape, or stalk me are statistically way too high too ignore.
Damn it, guys. We shouldn't have to keep explaining this to you. If you are a good man, then you will be taking our safety into consideration and not put us in situations like this.