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Writer's pictureJulie Kay

Bad dates (and the songs to accompany them)

If you've ever been on dating apps, you know there's an ebb and a flow to it. Sometimes it seems you can't get a date for the life of you, and other times, three dates materialize out of thin air! This weekend happened to be the latter, and let me tell you, it was enough to write off dating for good. But when it's enough to write off dating for good, it's good for my writing.



Shall we get started? I've categorized these evenings below.


The Date That Started Before I Got There

It's Friday night, and I'm looking forward to a drink to cap off a long week. I worked right up until I had to leave for the date, so decided that I'd walk the mile or so there to get some exercise. I arrived at Time Out Market at 6:00 pm on the dot, but because it was a sweltering 20 degrees outside, I needed a moment to thaw out. For those unfamiliar, Time Out Market is a food hall with communal seating - basically row after row of long tables. Every so often along the tables, there are divider signs (with cute quotes about Chicago!), and this helps to create natural seating areas for couples and groups. My date chose to sit behind one of these signs (cool) and already had a beer in hand (awesome). I thought, "Well this is awkward, how is he going to get me a drink now?" I guess he isn't. Wasn't. After the appropriate amount of dilly-dallying about with my coat and belongings awaiting the offer, I gave up and strode to the bar.


Now, I can understand grabbing a drink prior to your date arriving if he/she is upwards of 15-20 minutes late. I can understand not paying for your date's drink...actually, I can't really think of any situation where this is acceptable on a FIRST date. At least the FIRST drink. You might give a younger guy the benefit of the doubt, but this dude was 34 years old. And still lives with roommates, so it's not like he's even on the hook for the full rent!


Thankfully he had another commitment to get to (oh darn!), and I was left surrounded by an array of tasty food stalls. Mott Street saved the night with a:



Paradise is the sweet, sweet freedom that comes with two juicy beef patties sans forced conversation.


The Date That Never Ended The fun is just beginning! The scene is Saturday, second date, ice skating at Maggie Daley Park and then dinner. I know what you're thinking, "This sounds pretty darn good, Julie!" In theory, yes. But a snowstorm diverted our original second date plans, where I'm pretty sure I would've realized that there was not a lot more to this guy than work and the gym. What would have been an hour or two on a Thursday night turned into almost five hours on a Saturday night, and you know this is not the same thing. Sadly - I got the following - without the party bus, or the DJ, or the champs.



When we walked out of the restaurant at the end of the night, our masks were still on (as you do sometimes during Chicago winter). After chatting for a few minutes our Ubers showed up, and thus, the critical moment. He took off his mask and leaned in...and I turned and hugged. About 20 minutes later, when I got home, this text popped up: "Hey there, just got home! Had fun today and I'm glad you did too. But it seemed like we were both having more friendship vibes than relationship vibes. Really enjoyed getting to know you though and wish you the best!" Again, this seems pretty nice on the surface...but hear me out.


Look, no one wants to send THAT text, even if it's just a handful of dates. And if you are kind enough to send a text, rather than ghosting, you give it a little bit of time (whether out of pure avoidance, or because you're thinking of how best to say it, or whatever). Doing it *right* after the date tells me his ego was bruised and he wanted to have the final say. No matter how disinterested I was, it still doesn't feel very good to have received that message before I'd even put my leftovers in the fridge. It's like applying for a job and receiving the 'we've decided to go with another candidate who's better suited' email within five minutes of applying. Oof, there's still one more.


The Date That Ended in 35 Minutes

Saved the best for last. Before I start, I can't reiterate enough, LISTEN TO YOUR GUT. Especially when your gut tells you that you are not looking for someone who downs Monster energy drinks before going to the gym and tries to convince you it's the same as drinking coffee. With reluctance, I went to meet the man behind door no. 3, oddly enough, at Green Door Tavern. (Great bar, not sure I'll be able to look at it the same way again...) Pretty early on, I realized this was not going to be good. These are all types of 'not good,' by the way:


-nice guy, no spark

-not very nice guy, spark

-dissimilar interests, values, or goals

*and worst of all*

-lack of self-awareness


This guy was really out of touch, made tons of crass comments, and generally struggled to maintain any type of conversation. Honestly the best thing he did was go to the bathroom so I could flag down the waiter for the check. A telltale sign your date is a crash course? When your date ends before your parking meter expires. I don't think there's much more I can say here but:



Now I've never been great at math, but these are tough odds. Does one just throw in the towel? Or do you keep going, and hoping, knowing that there's definitely not a 33% chance for success? This is the no man's land I think many of us 'single' folks find ourselves in. You're damned if you do but 'don't' doesn't feel particularly good either. I don't have the answers, but all I know is I'm going to need a MOMENT after this one:



Hope you enjoyed the songs! Until next time...

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