- Jessie and Bertram first meet and he accepts her as their new nanny carelessly.
- Jessie askes 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 loud speaker 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.