Chulip!

I have a fondness for this game as one of the games that kind of comes from Love-de-Lic depending on how you look at it (like a branch from a tree).

If you like Moon RPG Remix, you'd probably like this game (you may or may not also like Chibi-robo).

You play as a boy, who has a dream about meeting the love of his life under the Lover's tree. After waking up, Him and his father move into Long Life town from the big city. Our protagonist and his father are quite poor, and this is the topic of the local rumor mill. This doesn't deter our protagonist however, as he sees the girl from his dream. 

He tries to win her heart but if swiftly rebuffed at first, for being a poor boy. On the advise of his father as well as a mentor figure he comes across, our protagonist works hard and kisses many people to strengthen his heart to being able to write a proper love letter.

There is a side plot about a telephone-poll person who is a disgruntled school teacher who has a fair point about paying your employees. This side plot becomes the main plot as our protagonist works towards being able to write a good love letter to this girl, but due to a series of increasing circumstances, our protagonist looses the love letter set and gets stuck trying to clear his family's name.

There's a lot of delightful characters in this game.