Fate/stay night - Season 1 - Eps 20: Distant Trace of a Dream
Shirou takes Saber out on a date to try and convince her not to use the Grail and go back to her own time, but to stay in this time instead.
About Fate/stay night

Title: Fate/stay night
First Air Date: 2006-01-07
Last Air Date: 2006-06-17
Status: Ended
Rating: 7.3/10 (from 209 votes)
Language: JA
Seasons: 2
Total Episodes: 24
Network: Teletama
Genres: Animation, Sci-Fi & Fantasy, Action & Adventure
Production Companies: Studio Deen, Notes
Synopsis
Shirou Emiya lost his parents in a fire when he was young and was later adopted by the sorcerer Kiritsugu Emiya. Shirou is drawn into the Holy Grail War summons a female "Servant" known as Saber to protect him and obtain the Holy Grail.
Cast

Noriaki Sugiyama
Shirou Emiya (voice)

Ayako Kawasumi
Saber (voice)

Kana Ueda
Rin Tohsaka (voice)