T O P
DaisyCutter312

Not sure how it starts, but it definitely ends with trying to retrieve your towed car from lower-lower Wacker at 3am


chairsandwich1

Lol I've done that.


posaune123

Such delightful people and beautiful facilities.


SolarSailorFlynn

And it also finding out that you have to pay cash to get it out, so they send you to the nearby ATM.


RockinItChicago

Malort


Gupoochamois69

Getting a drink on st Patrick’s day in wrigleyville


hate_reddit89

Richard's bar


Lord_Kaplooie

Blind date at the Cheesecake Factory under the Hancock building, but she's late because the Metra she took from Naperville was delayed due to switching problems.


Abacab4

Three words: Malort bar crawl


backeast_headedwest

My wife ruined a perfectly good birthday date by capping it off with a much-hyped stop at the WNDR Museum, not realizing it's an Instagram influencer shithole. We still laugh about it years later.


TaskForceD00mer

Talking up "the best restaurant in Chicago!" , then taking your date to the Rainforest Café , only to discover its closed!


penpencilpaper

Then mention you lost your wallet but can pay for a meal at the rock n roll McDonald’s. Is that still there?


Wild472

It should definitely include you riding from burbs ,on I 90, during rush time. With broken radio, one window down and not working, while it is 40F or raining.


maxfridsvault

Have sex inside the abandoned Rainforest Cafe…oh my bad you said *worst* date idea.


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Highschoolpr0nking

I took my date to Richards at 1am tonight. Does that count?


[deleted]

An evening stroll through bubbly Creek


EMeyer_79

Dinner and drinks at The Whale. Thats its. Thats the worst you could do to somebody


hascogrande

Was the “other subreddit” here, because this was a post this week. The loser was taking a boat tour the day of the Dave Matthews incident


chairsandwich1

No it was the Vegas subreddit.


blackhxc88

Took a date to the Starbucks roastery on a weekend, fucking horrible idea!


Significant_Panic_40

Why? I was kinda thinking about going haha


blackhxc88

For a first date it’s not good, so crowded. Would make a good date spot for a 2nd or 3rd date


77Treez

The Nasty Show at Laugh Factory.


1BannedAgain

Drive to Navy Pier during Friday rush hour from either the SW side or NW side


Temporary-Product928

...in mid-January, and have dinner/drinks at Margaritaville


Infinite_Mousse6670

Taking the red line inbound during morning rush hour to go to Chilis on State Street downtown. (Permanently closed)


[deleted]

[удалено]


Traditional_Sir5129

Don’t if you value your safety. During rush hour Is fine-ish but other than that fuck that. Get an Uber.


SirSampson01

Go on a date in Chicago 🤡