Gillian Jacobs swore off anything alcoholic when she was very little. The most she does is drink Red Bull.

But being a teetotaler proved detrimental to her dating life. Well, that was the case, at least when she was in acting school, struggling to balance different aspects of her newfound adulthood.

Jacobs had difficulty making boyfriends or even meeting decent guys when she was studying at Juilliard School.

The dating scene in New York, at least for her, was heavily dependent on being wasted, and she was always stone-cold sober when meeting guys. Her college years left her with nothing but brilliantly bad date stories to tell later in life.

Gillian Jacobs Struggled to Find a Boyfriend

A Pittsburgh native, Jacobs moved to New York to study at The Juilliard School in 2000. She had high hopes of becoming an actress, but the school only made her life more difficult.

Apart from squeezing her acting interests out of her, New York also made her miserable in her dating life. It just added to her frustration of having a strict mother who had many rules about her dating life and dress-ups.

This strict household caused her to be closed off from the teenage romance scene one was supposed to experience growing up, and that showed in her pursuit of romance after getting to New York.

"Before there were dating apps, people met in bars," she said during her Sad Hot Girls feature with Vogue in 2018. "And when you don't drink, you don't really go to bars that often."

Gillian Jacobs struggled to get a boyfriend while in college in New York.

Gillian Jacobs. (Photo: Instagram)

For months, all she did was smile at guys on trains until, finally, a friend said they would set her up with a guy.

So, in preparation, she dressed up the best she could and "chugged an entire case of Red Bull" because she was THAT ready to get something going with the guy.

The date was at The Box, a famous nightclub in New York City. She tolerated everything bad about the place because she thought she would "meet the love of [her] life" that night.

Her attempts at flirting or making conversation didn't seem to work. He wasn't even interested in her. But that all changed when they went to another bar. He was interested in her now because of a change in the setting.

This, too, wouldn't work out for her, as she and her few friends got kicked out of the bar because her friends started a fight that the whole club got involved in. Highly caffeinated but sober and in a not-so-romantic mood, she and the guy parted as friends.

Gillian Jacobs's Worst Date Ever

In another instance, she had a possibly worse date. As she would describe during her 'My Worst Date' segment on The Tonight Show Starring Jimmy Fallon in 2016, this "painful" date also took place in New York.

Her date, she speculated, might have read up on date ideas in New York on the internet as everything he suggested they do was pre-planned.

The date started with sushi at a questionable place, and then they went to a cliché dessert place called Serendipity. She hated both.

While getting there, they drove past a few strip clubs, at which he made a bad joke.

Then, after a few embarrassing hours roaming around, they finally decided to go home. He insisted on dropping her home, so she obliged even though she just wanted to get rid of him at this point.

After complaining that he could not find the way to her apartment, he creepily suggested she come back to his place, where his mother could cook her breakfast in the morning. She rejected the proposal.

And so, they somehow got back to her place, at which point, he "pretended" he forgot how to get to his place from hers. So, he came up to her apartment, which wasn't well-furnished because she was broke.

He messed around with her stuff for a while before she could get him out of her room. But he kept contacting her for weeks, thinking they had a special connection.

Something similar happened with another guy she was set up to meet. It was her dad who fixed a date with a family friend.

The guy, who was with a few of his friends, chose a cool bar in L.A. to visit for the night. She knew the owner, so she got them in.

But, once inside, they got drunk. She felt the need to drive them home, and she did.

During the drive, the guys couldn't even tell where their houses were. After many attempts, they got the location right, and they got out. The guy even had the audacity to ask her if she would get to San Diego with him, a request she denied.

This guy, too, thought they would end up dating and kept texting her for a couple of weeks.

Other than these, Jacobs hasn't really talked about her love life. She is yet to explicitly reveal if she has found a boyfriend after such traumatic dates. But she reportedly said in a 2017 interview that she had a partner who was "very creative."