Throughout seven seasons of New Girl, Jess Day had some amazing boyfriends but some awful dates. It seemed almost every time she went on a big date, multiple things went wrong. From unsettling reveals to unreciprocated declarations of love, Jess’s dating history is filled with awkward moments.
However, not all of her dates were regrettable. Occasionally, she had an excellent time hanging with her partner. Rarely did guys take her on big extravagant dates, but she didn’t require those things to enjoy herself, all she needed was good company, and to avoid mishaps. Here are the good and bad times of her dating life.
10 Amazing: Warm-Up Date With Nick
When Jess and Sam first became an item they agreed to keep things casual. However, Jess struggled to separate her feelings from sex. Schmidt suggested that she go to dinner with him, Nick, and Winston to make it feel like she went on a date before hooking up with Sam.
However, Schmidt and Winston had to bail, and left Nick and Jess to have dinner together. Despite the strange circumstances and the pair not being a couple, they actually had a sweet date. They got drunk on a thermos of wine that Jess snuck in and shared some fun banter.
9 Sucked: TinFinity Party With Jax McTavish
While she was on the lookout for a man who was willing to express emotions, Jess met a football player named Jax McTavish. She took him to the party Schmidt and Nick were throwing for their tenth anniversary of living with each other.
Initially, it was going well between the two of them until Jess realized that Jax was more emotional than she anticipated. He came on extremely strong and even publicly declared his love for her. It made Jess so uncomfortable that she hid from him for the rest of the party.
8 Amazing: Karaoke With Robby
Viewers never got to witness this date, but based on the story Jess and Robby told, it was fun. The pair went to sing Karaoke together, and when their names were called, they couldn’t figure out which song to sing. They ended up going with a song from The Doors and brought the house down (by their own estimation).
It didn’t sound like the craziest or most elaborate date in the world, but the enthusiasm they both showed while recounting it proved they had a wonderful time.
7 Sucked: Dice Date
Jess went on several bad dates with people she met on the dating app, Dice. However, the worst one was with a very strange and mysterious unnamed man.
He invited her to a food court, but when he revealed that he didn’t have any money, he took her back to his place. He then walked on a treadmill while staring blankly. Jess was very confused about everything that was going on, so she called Schmidt and asked him to rescue her.
6 Amazing: Prince’s Party
This didn’t begin as a date as originally Jess attended Prince’s party with Cece. Yet, before Jess left for the party, Nick told her that he loved her, and she didn’t say it back, so Nick followed them to the event to set things straight.
While there, Prince approached the couple and requested to spend some alone time with Jess. The musician then fed her, give her a new outfit, and taught her about love. Jess then returned to the party, at which point, it became more of a date between her and Nick. She declared that she loved him, and they sang and danced on stage with Prince in what was an incredible moment.
5 Sucked: Double Date Plus Winston
When Jess and Nick were an item for the first time, they planned on going on a double date with Cece and Schmidt, and they invited Winston along too. It had the potential to be a great night until Jess found out that Schmidt was cheating on Cece with Elizabeth.
Schmidt then desperately tried to stop Cece from finding out by keeping her away from Jess. Eventually, though, Schmidt was forced to come clean to Cece about what he’d done, and they broke up before they even sat down for dinner.
4 Amazing: Attended A Wedding With Nick
Not long after Jess and Nick met, they attended a wedding together. It wasn’t a real date, though, Jess just posed as Nick’s girlfriend to keep him away from his ex, Caroline. She was even given instructions on how she should behave during the event.
While this sounds like a bad date, it actually went really well by the end. Once Jess stopped following the gang’s rules and just let loose, she had a lot of fun. And after Nick got drunk, she shared a beautiful moment with him in a photo booth, and then all of the roommates participated in an amusing group chicken dance.
3 Sucked: Dinner With Russell At The Loft
In the early days of the relationship between Jess and Russell, they always stayed at his place. Wanting to mix things up, she invited him to spend a night at the loft, and it didn’t go well.
Her roommates acted really weird around Russell as Nick stole his noodles, and Schmidt made fun of his taste in sushi. It got even worse after Russell started drinking because he then ignored Jess and spoke with her loft mates instead.
2 Amazing: Bar Crawl And Dinner With Ryan
On Valentine’s Day, Jess and her boyfriend Ryan planned to go to dinner. However, Nick invited them to go on a bar crawl he had just finished organizing, so they did both.
The night didn’t start well for the couple, as Ryan’s suggestion that they move in together created some awkwardness. Once they talked through that, though, the two of them shared some sweet moments. It turned out to be an unconventional yet enjoyable date.
1 Sucked: Hiking With Robby
The realization that Jess and Robby were related came towards the end of their hike, and that alone confirmed it to be among the worst dates Jess ever had. But even before the reveal, the date was terrible.
It started to go wrong when they left the main trail and got lost. Finding and making their way back to the right path proved difficult too because Robby’s glasses broke, and Jess hurt her leg. After taking shelter in a cave for a while, they successfully made their way back, which was the only good thing to happen on an unpleasant date.
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