Andy: He'll sing 'Perfect' by Ed and plays guitar. After the song, he asks if you want to go on a date with him.

Rye: 

Brooklyn: 

Mikey: You played hide and seek together. You hid in his suitcase and tried to not make any noises. He searched everywhere and finally found you. You're a bit too clumsy for life and fell on him. He smiled and asked you out.

Jack: At his parents house, he asked you about your imagined best date and tell him about it. the very next day he asks you out on your imagined date you always wanted.