When Gillian Jacobs was a child, she swore up all alcoholic beverages. She only does one thing: she drinks Red Bull. However, being a teetotaler had a negative impact on her dating life. At least, that was the situation when she was in acting school, attempting to manage many facets of her newly acquired adulthood.

When Jacobs was at Juilliard, she had a hard time finding boyfriends or simply meeting respectable guys. The dating scene in New York, at least for her, was highly reliant on being inebriated, and when she met males, she was always stone-cold sober. Her undergraduate years provided her with nothing but hilariously terrible dates to tell later in life.

Gillian Jacobs Was Having a Hard Time Finding a Boyfriend

Jacobs, a native of Pittsburgh, traveled to New York in 2000 to study at The Juilliard School. She aspired to be an actor, but the school only made things more difficult for her.

New York not only suffocated her acting ambitions, but it also made her miserable in her dating life. It just added to her dissatisfaction with her strict mother, who had a lot of regulations about her dating life and how she dressed up. Because of her rigid upbringing, she was cut off from the typical adolescent romantic environment, which manifested itself in her search for love once she arrived in New York.

“People used to meet in bars before there were dating apps,” she stated in an interview with Vogue in 2018. “And you don’t go to bars very much if you don’t drink.”

While attending college in New York, Gillian Jacobs struggled to find a boyfriend. For months, she did nothing but smile at boys on trains until a friend offered to set her up with a guy. So, as part of her preparation, she dressed up as best she could and “chugged a full case of Red Bull” because she was THAT eager to start dating the guy.

The date took place in The Box, a well-known New York City nightclub. She put up with everything because she believed she would “meet the love of [her] life” that night. Her attempts to flirt or strike up a conversation failed miserably. He didn’t even care about her. But it all changed when they headed to another bar. Because of the change in the setting, he was suddenly interested in her.

This, too, did not work out for her, as she and her few companions were thrown out of the pub after her friends began a brawl that drew the attention of the entire club. She and the gentleman parted as friends, highly caffeinated yet sober and in a less-than-romantic mood.


The Worst Date Ever for Gillian Jacobs

She had a possibly worse date in another instance. This “awful” date took occurred in New York, as she described it during her ‘My Worst Date’ segment on The Tonight Show Starring Jimmy Fallon in 2016. Her date, she reasoned, might have looked up date ideas in New York on the internet because everything he recommended they do was prepared ahead of time.

The evening began with sushi at a dubious establishment, followed by a trip to Serendipity, a cliché dessert joint. She despised both of them. They drove passed a couple strip joints on their way there, when he made a stupid joke.

They ultimately decided to go home after a few humiliating hours of wandering around. He insisted on dropping her off at her house, so she did so, despite the fact that all she wanted to do at this point was get rid of him. After lamenting about not being able to find her apartment, he made the creepy suggestion that she return to his house, where his mother could prepare her breakfast in the morning. She turned down the offer.

So they made it back to her apartment, where he “pretended” he forgot how to go back to his place from hers. So he came up to her flat, which was sparsely furnished due to her poverty. Before she could get him out of her room, he fooled around with her belongings for a time. However, he continued to contact her for weeks, believing they shared a particular bond. Another guy she was supposed to meet had a similar experience. Her father set up a date with a family friend.

The guy chose a cool pub in L.A. to spend the night with a group of his buddies. She was able to get them in because she knew the owner. However, once inside, they were inebriated. She felt compelled to drive them home, which she dutifully did. The boys couldn’t tell where their dwellings were during the drive. They finally got the spot right after numerous attempts, and they were able to leave. He even had the arrogance to ask if she would accompany him to San Diego, which she politely declined.

This guy, too, believed they’d wind up dating and texted her for several weeks. Other than that, Jacobs has been tight-lipped about her personal life. She has yet to say whether she has found a boyfriend following such painful experiences. However, she reportedly stated in a 2017 interview that she had a “very creative” spouse.


By Meera