This Bachelor Party-Goer Became an Instagram Legend with His Sad Tourist Shots



For many, bachelor parties serve as an opportunity for a group of friends to experience one last hurrah together. Robbie Chernow expected to do just that and have a weekend full of fun to celebrate his friend Jake’s bachelor party in Chicago. That all changed when the 28-year-old arrived in the windy city on Thursday from New York City on a JetBlue flight. His unlucky group of friends had their Delta flights canceled to Chicago from the big apple, which left Chernow completely alone in the windy city.

Carousel for one. Chernow shared the image of himself before he enjoyed a solo ride on a carousel.

Gloom. Chernow shared the image below on Instagram when he realized he’d be enjoying the NFL preseason game . . . friendless.

Empty seats. The 28-year-old also took in a boat cruise and shared the photo below of him being surrounded by empty seats that should have been filled with his friends.

Chernow decided to create the hashtag ChicagoForOne, in an effort to detail his journey and experiences in the city on Instagram since he decided to stick with the scheduled plan of events. In almost every photo he posted on Instagram at the various stops he made, Chernow appeared to look pretty sad.

The Pennsylvania native kicked off the trip by going solo to enjoy a preseason Chicago Bears game. He also took in a boat cruise, a spin on a carousel, visited the world-famous bean, and met a ton of strangers who took pity upon his sad situation. Chernow, who is a member of The People’s Improv Theater, even turned to the notorious dating website Tinder, in hopes to meet a friend to enjoy the city with.

Robbie Chernow was expecting to enjoy a bachelor party trip to Chicago with his friends until their flights were canceled and he was completely alone in the city. Below, he smiles while holding a Chicago Bears game ticket.



Chernow created the ‘ChicagoForOne’ hashtag on Instagram to share his solo experiences and journey in the windy city. He is pictured with two women who gave him a Bears schedule magnet.

He wrote on Instagram that it was his first time swiping right and left on the site. More importantly, he explained that he was not trying to use Tinder for sexual purpose, that he was just simply “looking for a friend.” Chernow took a screen grab of a message he received from one user on Tinder who inquired with him about his skill level in bed and shared it on Instagram saying, “It got weird real quick.” One of the brown-haired gents’ friends felt so bad for him that he created a GoFundMe page to help lift his spirits.

No fun. Chernow shared the photo below in which he appeared to look sad while on the boat with Chicago’s famous skyline in the background.

New friend. Chernow shared the image of below on Instagram where he captioned that the woman named Michelle sat next to him and showed “genuine remorse” for his situation.

Beef sausage. In the photo below, Chernow stood with his new friend Theresa whom he met at Portfillo’s. He says that the woman said he seemed “sad enough” to finish an Italian beef sausage sandwich on his own.

The bean. The lonely guy took a selfie in front of the famous Bean at Millenial Park.

The bean: The lonely guy took a selfie in front of the famous Bean at Millenial Park



Water ride: Chernow shared the image below, stating that the captain of his water taxi, Ray (left), insisted that he wear a life vest to “ensure” his safety.

“I’ve had 2 days to experience this firsthand, and now I’m asking that you show the bachelor the same hospitality! He’s been cooped up in a hotel in Queens since yesterday and now only has 48 hour to make up for lost time!”

Surprisingly, the fundraising efforts exceeded the $250 goal by raising more than $420 in donations.

Collection plate. Will Heineman, one of Chernow’s friends, felt bad for him, so he created a GoFundMe campaign to raise ChicagoForOne Funds on September 4.

Collection plate: Will Heineman, one of Chernow's friends, felt bad for him so he created a GoFundMe campaign to raise 'ChicagoForOne Funds' on September 4 

Surprisingly, the fundraising efforts exceeded the $250 goal by raising more than $420 worth of donations for the #ChicagoForOne Funds. Chernow posted a photo of his friend Jake hugging him after the rest of the group finally arrived in Chicago on Friday. “I’d like to thank everyone for their unwavering support in my time of loneliness,” he wrote in the photo’s caption. “Chicago is an amazing city with even more amazing people.”


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