On May 12th, Madison's dad kept talking about setting her up with Ian, because Ian's father is one of Madison's dad's co-workers. Madison was freaking out about it, because, although she loves her dad, she didn't want him to play matchmaker for her.
Madison became interested in Ian when she was told Ian played guitar. Madison thought about going to listen to music with Ian, or asking him for guitar lessons.
Madison talked to Nolee on May 17th about Ian, but was unsure if Madison should agree to go on a date with him until she found out more about him. Nolee hoped Ian would be a Libra, because Libras supposedly get on well with Leos, like Madison. Madison asked her dad for a photo of Ian, as well as some more information about him. She found out that Ian also played in a band.
Madison finally went on a date with Ian on June 3rd, and they met up at a movie theater in the East Village and then watched some live music. Madison found out that Ian plays in a band, and she thought he had a great smile. She also liked his style, which she referred to as "hipster thrift store duds". She wrote that she definitely had fun with Ian, and thanked her dad for setting her up with him.