Most of the time, Italy and England don't talk with each other unless it is war interactions, usually just when either one of them are in captive of the other because of Italy being a major power in the Axis and England in the Allies. They have spoken in the comics though and do sort of get along at least after World war II.
World War II (Main Timeline)Edit
Italy was captured several times by the Allies in Episode 08, and this is where England offers to feed Italy. However, Italy refuses it, stating that it was terrible food, which upsets England as if he actually took into care of what Italy said.
African War FrontEdit
In Episode 126: African War Front! Part 1, Italy is going to Africa and England intercepts this piece of information and wants to capture him, saying that he'll bow down at the feet of the British Empire. After claiming those word, Italy appears suddenly while dressing as an elephant. England is stunned for a second as Italy tries painfully to imitate an elephant but England isn't fooled and gives chase to Italy, making him shrieks out of horror.
As England tries to outruns him, Italy has managed to suppress his power and runs away from England. .
This pairings was started because of the infamous HetaOni fan-game where several nations are trapped in a mansion with no way out and a monster out there to kill them. Italy is the main character of the game, and he's the most traumatized one as in the first timeline, he watches as everyone died and left him to escape alone. After that, when a nation dies, he decides to rewind time back with a journal he finds to make sure all of them could escape alive.
In England's case, in one of the timelines, he has overexerted his magical power to defeat the monster and sacrifices his eyesight, which is revealed by America as he asks England how many fingers is he holding and England apologizes, answering that he can't see anymore.
It is worth mentioning that in the timeloop where Italy died, England rewinded time to save him.
Due to these events, they are called the Angel Pair. In Hetaoni, England/North Italy are considered canon by some. However, this has not been explicitly said.
Fans believe that England and Italy would be a good pairing due to them being exact opposites: England is bad at cooking while Italy's good, Italy acting stupid and silly and innocent while England is very serious and far from innocent.