September 2017—The Time A Guy Expected Me to Drop Everything for Him

When I decided to move back to Chicago at the beginning of 2017, I threw in the proverbial dating towel in Oregon. I figured the other single women of Portland could have all the hipsters, baristas, and anyone else who had moved to the city to “find themselves” or “work on their art.”

So, I stopped looking for love in the City of Roses and moved back to Chicago. This did, however, meant having to wade through a new dating pool.

Not my favorite.

Let me be honest. Going on dates is time-consuming and tiring. I show up, plaster a (hopefully) pleasant smile on my face, and cross my fingers that whomever I’m meeting is a decent human being who can hold a conversation.

This sounds like it should be easily met, but you’d be surprised how many people haven’t learned the art of conversation.

A few months after moving to Chicago I met Craig. On paper, he was a great match. He was an Assistant Professor at the Northwestern Medical School who enjoyed traveling the world, cycling, and science fiction (namely Star Wars). The banter between us was great and we were able to talk on a variety of subjects.

Finally, someone to use all my useless knowledge on.

Now, my father has always told me that no man is perfect and that I would need to accept this or be single forever.

Great advice, Dad.

And while there are certainly imperfections one can ignore or compromise on, sometimes this isn’t the case.

My issue with Craig is that he had absolutely no concept of planning and I’m an organizational Type A personality.

So not the best match perhaps.

Over the years, I have accepted that not everyone is obsessed with their calendar or finds scheduling fun, but I would say that most people are considerate enough to give a day’s notice when making plans. The problem with Craig and I was we had differing schedules: I worked an 8-5 and Craig enjoyed an academic schedule that only required him to be on campus a few hours a day (I remember those days…). Coupled with the fact he didn’t live in the city, planning was crucial since we couldn’t just meet up on a whim.

But Craig didn’t seem to understand that.

For our first date, Craig wanted to grab dinner around downtown Chicago.

“Great!” I responded. “I’m open every day but Tuesday this week at the moment.”

I’m poised, at my phone, ready to block off an evening for dinner as I wait for his answer.

His response? He says he’ll let me know but “maybe Wednesday.”

Ugh. That’s one of my least favorite planning phrases. It’s basically saying, “I might be available that day, but if something better comes up, I’ll go to that.”

It’s so Millennial.

So, I “tentatively” block off Wednesday in case Craig wants to do something. We continue to text over the next few days and he finally confirms he’ll be available for dinner on Wednesday. However, he’ll let me know what time later as he has a happy hour Wednesday afternoon for new students “but he’ll probably be done around 5:30 or so.”

OMG, can this guy commit to anything?

Maybe this is why he’s still single?

So, on Wednesday night, I get home with still no idea when I’ll meet Craig for dinner.

This is way too much work for a first date.

I putter around my apartment as I wait for Craig to text me. I get one around 5:30 but it’s not what I’m expecting. It seems like the happy hour will be longer than expected but that I’m “more than welcome to crash it.” After all, “I look like one of the students.”

…thank you?

I decline the invitation and ask him to let me know when he’s done and where he’d like to meet up. He tells me to pick something.

Oof. Okay. You’re the one who asked me, shouldn’t you be picking the venue?

While I continue to wait on Craig I look for somewhere to eat and (finally!) around 6:30 Craig finally tells me he’s done schmoozing and can grab dinner.

Since I’m farther away from the restaurant, I quickly make my way there.

And I still have to wait on him for ten minutes.

He’s definitely not winning any points with me.

Craig and I grab dinner and the affair is pleasant enough. Our conversation is just as good in person as it is over text. When we part for the evening, Craig queries about my schedule for the rest of my week. When I tell him I’m leaving for New York in a few days for a weekend trip, he asks if I want to do something the next day. I tell him “no” as I already made plans for that evening.

But Craig seems to take this as, “But you have a few hours after work to hang out before your event, right?”

No. That is not what I’m saying. I’m telling you I’m already committed to something else and we can see each other once I’m back in Chicago and my schedule is free.

When we part for the evening, Craig is still insisting we get together the next day and that he’ll “text tomorrow to figure out what time.”

Did he listen to anything I said?

The next day, Craig reiterates getting together that evening “even for a little bit” since he doesn’t want to wait until I return from New York.

Am I supposed to take it as a compliment that I apparently infatuated him so much that he wants to see me all the time? Cause I’m just getting annoyed that he keeps dodging the question of planning another date the next week.

He keeps trying to convince me to see him that evening but only as it relates to his schedule. Craig tells me he has a function that evening until 5:30 but explains he’ll be free at 5:30. Since my meeting isn’t until 7, we’d have an hour to spend together before I’d have to leave.

Yes, because the last time he said he’d be available at a certain time he made me wait for an hour.

Academics really have no concept of time, I swear.

It’s becoming apparent that Craig seems unable to schedule something more than 24 hours in advance and when it does come to planning to see each other it has to fit in with his schedule.

Unfortunately, I’ve come down with a bad cough and I sound like I’m dying. Coupled with the fact I’m traveling the next day, the best thing for me to do is stay home and go to bed early, not go out.

Craig doesn’t seem to understand this. After all, he “only wants to see me for a little bit.”

Dude, I feel disgusting. I am not dragging myself out of my apartment, plastering a fake smile on my face, and hoping I don’t hack up a lung just to appease your need to see me for “a little bit.” One date does not a relationship make.

Even though Craig’s pestering makes me want to strangle him, I don’t want him to think it’s I don’t want to see him again at all. So, I ask about his schedule the next week so we can plan something for when I return to Chicago. He says he doesn’t typically stay downtown past the late afternoon so he doesn’t have any evenings the following week that would work.

Um, okay. For someone so adamant about seeing me right this minute, the refusal to make a date for a week’s time is sending some mixed signals.

Because apparently staying on campus for another couple hours until I get off work so we can grab dinner is such a hardship. You have a private office. Take a nap or read a book to pass the time. Hell, visit the art museum. You can’t be bothered to wait around for a bit but I’m supposed to rearrange my schedule for you? Seriously?

Craig’s tone and his continued, “Are you sure you can’t come out tonight?” texts are making me the cruel and uncaring person in this conversation because I’m barely functioning and won’t see him that evening. I have a hacking cough and all I want to do is make some soup, put on a pair of yoga pants, and watch Netflix.

Trust me, no one wants to see the hot mess I was resembling on my couch, especially a guy who’s only taken me out once. Even my roommate looked like she was seriously debating putting on a hazmat suit after hearing me cough.

Being sick is no joke.

I finally put my metaphorical foot down and tell Craig I’m not leaving my apartment and that we can make plans for when I get back and feeling better. He finally acquiesces. We text a few times while I’m in New York and then radio silence. No response to my texts.

Alright, I can take a hint.

I’m sorry my undesire to pretend I’m not dying of a communicable disease was apparently not a good enough excuse not to see you. Or that my preference to schedule something rather than “playing it by ear” on a day you might want to see me wasn’t preferable. Or how staying in the city for an evening seemed like such an inconvenience.

Goodness. What would it have been like if we’d have actually seriously dated?

I think it would have made me a harebrained mess.

Hard pass.

I’ll wait for a guy who appreciates the art of planning. I’d rather keep my sanity in check.

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