Instagrammer Chronicles The Saddest Chicago Bachelor Party Ever

By Rachel Cromidas in News on Sep 8, 2015 5:45PM

Labor Day Weekend was full of weddings, reunions, air travel and other last-ditch efforts to savor summer—and with them, the massive flight delays you might expect.

A slew of flight delays left one unlucky New Yorker in Chicago for a friend's bachelor party getaway utterly alone when none of the other men in his party could make their flights. Robbie Chernow, 28, decided to turn his unexpectedly solo-visit to Chicago into a one-man tromp through the bachelor party's itinerary, and chronicle the whole thing on his Instagram account in a series of morose and hilarious selfies.

"Hey @notjake_fromstatefarm, thanks for inviting me to your bachelor party and then having your flight get canceled so I'm the only one here! Let's go Bears! #chicagoforone," Chernow wrote on Instagram Friday as he kicked-off the bachelor party for one with a trip to a Bears game.

it only gets sadder and more comical from there as Chernow proceeds to take a lonely boat tour on the Chicago River and snaps a particularly distressed-looking photo in front of the Navy Pier carousel—along with a passive aggressive jab at the groom-to-be who could make it to his bachelor party.

Chernow met some helpful Chicagoans along the way, including a Portillo's waitress and a John Hancock Tower attendant...

This is Michelle. Her and her family sat next to me on the boat (the seats that my friends would've been occupying had they made it here). She showed genuine remorse for my situation - So much so that she gave me a mini bottle of Cabernet before telling her kids "let's go sit somewhere else and let the sad man be alone". Thanks, Michelle! #chicagoforone

A photo posted by Robert Chernow (@rwchernow) on Sep 3, 2015 at 4:41pm PDT

This is Audrey and Nicolette. Even though I didn't sign up for the Master Card they were promoting, they still gave me a Bears schedule magnet because they felt bad and as Nicolette said "this will look good on your mini fridge. (Beat). You seem like someone with a mini fridge". Thanks, Audrey & Nicolette! #chicagoforone

A photo posted by Robert Chernow (@rwchernow) on Sep 3, 2015 at 6:57pm PDT

This is Ray. He was the captain of my water taxi. After hearing my story he insisted I wear a life vest to ensure my safety. Accordingly to him "you must live in order to keep the bachelor party dream alive". Thanks, Ray! Sidenote - as apropos as it is that I'm literally blue in this picture, that was a random coincidence, not an added filter meant to illustrate my current mood. #chicagoforone

A photo posted by Robert Chernow (@rwchernow) on Sep 3, 2015 at 7:48pm PDT

This is Theresa. She works at Portillo's (which I've been told on Tinder has the best italian beef sandwich in town). According to Theresa, "these sandwiches are normally meant to be shared, but you seem sad enough to finish one by yourself". Thanks, Theresa! #chicagoforone

A photo posted by Robert Chernow (@rwchernow) on Sep 3, 2015 at 8:51pm PDT

This is Chad. He's the ticket agent for the 360 Degree Experience at the John Hancock Tower. According to him "the panoramic views of the city are unforgettably breathtaking...except when the fog rolls in...like this morning". Thanks, Chad! #chicagoforone

A photo posted by Robert Chernow (@rwchernow) on Sep 4, 2015 at 7:15am PDT

According to their website, the Wiener Circle is where "famously surly staffers dole out char dogs & more". That should have been my warning. Thanks for the self esteem boost, Wiener Circle! #chicagoforone

A photo posted by Robert Chernow (@rwchernow) on Sep 4, 2015 at 3:03pm PDT

...And he tried his hand a meeting people on Tinder, with disastrous results:

First time using Tinder! Fingers crossed! #chicagoforone

A photo posted by Robert Chernow (@rwchernow) on Sep 3, 2015 at 4:50pm PDT

Tinder update! It got real weird real quick. Think I'll stick to asking for recommendations from the hotel concierge #chicagoforone

A photo posted by Robert Chernow (@rwchernow) on Sep 3, 2015 at 7:14pm PDT

Chernow was at times so alone, he somehow managed to get a photo of his reflection in the Bean without any other people in it:

Both my hotel concierge Alex and new friends on Tinder agree - The Bean at Millennial Park is a must for a great photo-shoot. "It's the perfect for spot for a wacky photo with all your friends in front of the Chicago Skyline". Thanks, Alex! #chicagoforone

A photo posted by Robert Chernow (@rwchernow) on Sep 4, 2015 at 5:47am PDT

Chernow's sightseeing, stunts and Instagram hasthag earned him international attention by the weekend's close. Personally, we're proud of Chicago for showing Chernow a good time, and wondering whether #ChicagoForOne will get any follow-up acts.