Ore no Polaris

Wanting to change his lack of initiative, college student Meguru starts a part-time job as a "substitute traveler." He is asked to do unexpected things, from finding someone's first love to taking a stuffed animal along on a trip. Everything is a bit of a challenge, and things don't always go as planned, but Minami, his training supervisor, is always there to gently guide him through the process. But Meguru realizes his feelings toward Minami gradually changed from admiration to love...

(Source: Tokuma Shoten, translated)