Jessi is rather unlucky when it comes to love. She has been in some relationships with other characters, but she has a tendency of dating guys for the wrong reasons..

Nick Birch (ex-boyfriend)

Jessi has had a crush on Nick since the first episode of the series. She expresses annoyance at Olivia, Nick’s date for the dance, calling her shallow, vapid and brain-dead. Nick is oblivious to Jessi’s jealousy, and doesn’t see her as anything more than a friend. When Olivia ditches him, Jessi takes the opportunity makes her interest in Nick known. While comforting him, she can’t help herself from gloating about how she accurately predicted that Olivia was no good for him. She then compliments Nick’s hair style before initiating her and Nick’s first kiss. Their inexperience makes the moment awkward and as the kiss progresses, Jessi shows signs of discomfort. Nick, on the other hand, remains oblivious. When Matthew asks about their kiss at the end of the episode, Nick and Jessi prefer not to speak about it, which causes Matthew to believe that Nick fingered her.

By the time the day of the school field trip to the Statue of Liberty arrives, in “Everybody Bleeds”, other students have heard about Jessi and Nick’s kiss and assume they’re dating. Jessi and Nick tentatively affirm the rumor. Caving into peer pressure, they sit in the back of the school bus where couples such as Devin and DeVon are seated. Jessi and Nick struggle to act as a couple, with Jessi being more uncomfortable than Nick. Concerned about their awkwardness as a couple, Nick asks DeVon for advice. DeVon tells Nick that in order to be a good boyfriend, he needs to be physically close to her at all times. Nick takes this advice to heart and tries to spend more time with Jessi. Meanwhile, Jessi has been dealing with her period. She eventually confides in Andrew for help. This incites jealousy in Nick when he witnesses them embracing. Fortunately, he becomes understanding when Andrew explains that he was helping Jessi with her period.

Important to note is that the episode begins with Nick and Jessi sending each other humorous videos. Their dynamic here is relaxed, as opposed to their stitled interaction when dating. This foreshadows their eventual realization that they are better off as friends.

Their relationship comes to an end in “Am I Gay?”. On a date, they have difficulty carrying a conversation. Connie interrogates Jessi on her feelings, and Jessi admits that the kiss she had with Nick didn’t make her feel much. Jessi then decides to break up with Nick by letting him down gently. She tells him that they should be friends again. Unfortunately, Nick doesn’t take it as a breakup, and thinks that Jessi is still interested in him. It’s not until Leah explains it to him that their breakup registers with him. He seemingly takes the realization well. However, when interviewed by Matthew, Nick falsely claims that he broke up Jessi, indicating that he was hurt by being dumped by her. His dishonesty regarding their relationship angers Jessi. With Connie’s encouragement, she insults Nick’s big mouth in front of a crowd of students. They avoid each other for most of the episode until Andrew forces them to reconcile. The pair admit that they prefer being friends and remain as such for the duration of the series.

Jay Bilzerian (ex-boyfriend)

Jessi Jay First Kiss screenshot

Jessi french kisses Jay at Leah’s high school party.

Jay has had a crush on Jessi for some time in season 1, and has been flirting with her since at least “Girls Are Horny Too”, with her often expressing annoyance at his crude personality. In “The Head Push”, Jessi french kisses Jay after drinking some Cotton Candy Brandy. She makes him promise not to tell anyone about their kiss. The two officially begin dating in “I Survived Jessi's Bat Mitzvah”. In “The Pornscape”, Jessi, fed up with her parents fighting, decides to run away and elope with Jay. The pair are then seen hitchhiking in the season 2 premiere. During their trip, Jessi ends up meeting Pam. Jessi then becomes disgusted upon learning about Jay’s sexual relationship with his pillow. This is when she begins to doubt their relationship.

Jessi Jay Motel Fight screenshot

Jay fights and breaks up with Jessi at the motel.

The moment that broke the camel’s back for her was when they were making out in a motel, and Jay wanted her to engage in his fantasy where he is a forty year old magician and she is presumably thirteen. This thoroughly disturbs her and they have a fight about it, Connie further worsens Jessi’s fears about the relationship by telling her that she’ll end up as “one of those weak women who goes for bad guys with stupid brains and garbage dicks!”. All of this prompts her to break up with Jay, and the feeling is mutual. When Andrew and Nick find out about their breakup in “What Is It About Boobs?”, Jay calls it “fake news”.

Despite having entered a relationship with him, Jessi was hesitant to be known as Jay’s girlfriend, whereas Jay, on the other hand, wanted to introduce her as his “very serious girlfriend“ right away.

Judd Birch (crush)

In season 3, Jessi develops a crush on Judd. She is weirded out at first due to his violent personality, and him being her friend’s brother. The first instance of her attraction to him is in “How To Have An Orgasm”, where he is the focus of her sexual fantasies. Jessi eventually receives her first orgasm while masturbating to him. Prior to this, they had little interaction, yet Judd still knew who she was. The few times Jessi tries to talk to him, she ends up tongue-tied and flustered. When the girls make their list in “Rankings”, Jessi is disinterested in any of the middle school boys, preferring Judd because he is older. She is simultaneously intrigued by Judd’s maturity while also being appalled at his intensity. At the wedding, Jessi musters up the courage to offer to dance with him. She ends up being rejected by Judd on the basis that “[he doesn’t] dance with kids”. This prompts Jessi to ask Connie if she’ll grow out of “liking guys [she] can’t have”, to which Connie is unable to properly answer.

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