Bessie (B/ertram and J/essie) is the friendship pairing of Jessie Prescott and Bertram Winkle. They first meet in New York, New Nanny. Bertram tries to act like he can care less about Jessie at first, but deep down inside, Bertram really does care about Jessie and the Ross kids.
- Jessie and Bertram first meet and he accepts her as their new nanny carelessly.
- Jessie asks for Bertram's advice on what to do when she wants to be Luke's paintball partner without babying him.
- Jessie knows that Bertram sticks his head in the pantry and pretends to inspect cheese when he gets scared.
- Bertram helps Jessie when her hair gets stuck in the tree, and, appears to be a little concerned.
- Bertram tries to help Jessie assure Ravi that Santa Claus is a good guy.
- Bertram dresses up as Santa Claus in order to aid Jessie in trying to get Ravi to stop being afraid of him.
- Bertram decides to help Jessie get the tiara back.
- Bertram agrees to go on a date with Mrs. Chesterfield in order to get Christina's tiara back, and, protect Jessie from getting fired.
- Bertram tells Mrs. Chesterfield that he wouldn't even be in her apartment if she had given back the tiara, so, he obviously did it to help Jessie (and Zuri).
- Bertram says no one can call Jessie and the kids names but him.
- Bertram turns on the loudspeaker in the kitchen so Jessie can hear Brody talking to his other girlfriend.
- Bertram (and Emma) help Jessie prepare for an audition.
- Bertram says he wanted to be the one to slap Jessie with the ruler.
- Bertram and Jessie rehearse the lines together.
- They almost kiss, but turn away in disgust and say that it's enough.
- They both agree that the penthouse has become more quiet than usual.
- The Ross kids saw through the security cameras and thought they were dating, much to their horror.
- Jessie tells Bertram she is freaking out about her dad's wedding.
- Bertram (and Corporal Cookie) turn on the blender so no one will hear Jessie.
- They both tried to pull Luke out of dance class.
- They were both invited to join Luke's class (unaware it was merely an accuse to keep Luke in class).
- They were seen crying next to one another when the instructor cut them out due to their bad dancing.
- They danced together in front of the Ross kids at the end of the episode.
- Jessie tackles Bertram when she catches him spying on her.
- Bertram admits to Jessie that Mrs. Chesterfield is blackmailing him into digging up some dirt on her.
- When Jessie considered breaking up with Brooks so as not to have him live poorly as an elevator operator, Bertram was saddened and looked like he didn't like the idea.
- Bertram convinces Mrs. Chesterfield to accept Jessie and Brooks' relationship, showing he obviously cares about Jessie's happiness and that he ships Bressie.
- Bertram was the first to know about Jessie and Brooks' engagement.
- Jessie comes to Bertram for advice about whether or not Brooks is "the perfect guy".
- Jessie was worried when Bertram got electrocuted because his kite got struck by lightning.
- Bertram defends Jessie when the Ross kids acted selfishly about her leaving for Africa.
- Bertram walks Jessie down the aisle on her wedding day.
- Jessie looked offended that Bertram was eating from her wedding cake after her breakup with Brooks, much to Bertram's embarrassment as he asks if it's too soon.
Zuri: Look Bertram! I found a new nanny in the street, can we keep her?! Bertram: (sarcastically) Congratulations, you just made the first cut!
Jessie: I made everybody some cookies. Where is everybody?
Bertram: I think they ran away because they hate you.