Once you have enough successful dialogues with the character, a message letting you know that they are your love interest will appear and you will be able to date them.
To have a successful date you will need to raise the Mood to 5/5 and kiss the character.
Gifts are a great way to increase your Relationship EXP.
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After buying 4 roses, Aiden will give you a shovel.
Go to The Wood past East Street and click on the ground to plant a rose in the soft soil. Once 12 are planted leave the area and come back to Raine will appear.
Talk to and give gifts they like to raise the Mood to be full in order to kiss.
Some characters have special cut scenes that play on your first date with them.
The cheat code gardeningisforsquares can also be used to unlock Raine.