Jake
Caroline first meets Jake when he tries to get a cup of tea out of the vending machine. She helps him by telling him that he has to stick a finger up the machine to make the milk come out, and embarrassingly ends up wiggling her middle finger at him.
She meets Jake again after she breaks things off with Mac, in the belief that Mac should have the opportunity to focus on fatherhood with Holly. She asks Jake to make her forget about Mac, and Jake claims she is confusing reality with the film Eternal Sunshine of the Spotless Mind. Jake however does the job, and it seems to work.
After meeting her again in the canteen, Jake asks her out. Guy overhears, and tries to stop him, but fails. When they do go out, the night goes badly: Caroline accidentally kills Jake's beloved 12-year-old tamagotchi by dropping it in a glass of wine, and Guy successfully throws a Swiss Army Knife at Jake's head. When Holly's lie about Mac being a father is revealed, Caroline breaks things off with Jake.
Read more about this topic: Caroline Todd (Green Wing Character), Relationships