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Ranking Jess Day’s 5 Most Notorious Boyfriends

Like most of us, New Girl’s Jess Day has been through her fair share of boyfriends. From the fancy rich man to the charming british teacher, Jess has experienced them all. While all men in her life, whether they were there for the long haul or just an episode or two, have taught her important lessons, you’d be lying to yourself if you said you didn’t have a favorite beau of Jess’s. This is my ranking of Jess Day’s 5 most notorious boyfriends.


Russell was one of Jess’s earlier boyfriends but stuck around even till the last season sporadically. As a father of one of Jess’s students, he made himself well known as the fancy rich man who seemed to have his whole life figured out, except for maybe his love life. Either way, Russell was a big switch from her previous, more immature boyfriends, and she loved it. Being whisked away into the extravagant world of ribbon-bow cutting appearances and staying at Russell’s lavish home seemed to be everything and more Jess could want in a man. However, in the long run they were not as compatible as it first showed due to their different hopes for their futures. 


If you’re a fan of New Girl, you either love Robby or you hate him. Personally, I’m not a fan, which is strange considering he is as close as it gets to the male version of Jess. Despite what I think of the strange and quirky guy, Robby was always a true gentleman to Jess. Perhaps, Robby was the most interested in Jess and pursued her in the most romantic ways. What started as a deep friendship turned into a great romance story, but things came to a sudden halt when it was discovered that the two are actually related. Yep. Related. Maybe that’s why they resemble each other so much. 


Now to my personal favorite, Sam. The dreamy doctor was my favorite boyfriend of Jess’s. Maybe because it was the most chaotic (which I tend to find the most relatable), or maybe it was just because I find Sam extremely attractive. Either way, this relationship seemed to be the most relatable to young viewers because the entire relationship was extremely messy. Extremely messy, like restraining order messy. The pair started through a web of lies, morphed into a friends with benefits situation, then into a committed romance which dissolved due to a kiss between Jess and her roommate and then back into a romantic partnership months later. Although Sam may not have been the one true match for Jess, it’s safe to say that the two shared undeniable chemistry.


Ah, the British dreamboat. Ryan was nearly perfect, especially for Jess, until the end of their relationship. I guess distance does really test a relationship because these two seemed as though they could have lasted forever, and if it hadn’t been for Ryan’s move across seas they might have been able to. Ryan, a british teacher, and a cute one too, treated Jess with respect and love unmatched to a lot of her past boyfriends. What started as a forbidden love, due to their work relationship, became one of the most important relationships for Jess. However, not even the british charm could justify the ‘ghosting’ he put Jess through at the end of the relationship and ultimately it was good that they ended. 


FINALLY! We’ve made it to our king Nick Miller, thank you. Thank you for caring for Jess since day one. Thank you for looking out for her even when you weren’t together. Thank you for putting her happiness above all else, and thank you for providing such high expectations for me as I look for my next boyfriend. When we first met Nick, he wasn’t all that impressive. A guy who failed out of law school and seems to have an unnecessarily hard time expressing himself in a healthy manner. Nothing too special, right? No, not right! As the series progresses, we see Nick as the one who is always there for Jess. He has one of the best character developments on the series and we watch him slowly open up to Jess. Self-confidence issues, boy problems, or simple daily malfunctions, Nick was always the first person to help Jess when she needed it. Nick and Jess’s relationship taught New Girl’s viewers that love has a pretty weird way of working, but what’s meant to be, will be. 

I don’t know about you, but I’m about ready to go binge the entire New Girl series right about now. Through the chaos, the romance, and everything in between, New Girl does an impeccable job at showing us the true realities of dating, but no matter how crazy your love life may get, never stop holding out for your Nick Miller. 

Kirby Tock

Wisconsin '23

Kirby is a sophomore at the University of Wisconsin- Madison who is currently studying Communication Arts. In her free time, she likes to stay active, watch New Girl, and hang out with her family, friends, and two dogs.
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