Talk:Perfect Match, Book 2 Choices/@comment-28690119-20181108051136/@comment-36836718-20181108123541

Yes, you need the outfit AND you have to talk to Winona's best friend. If you do so, you get to talk to Ryan Summers and he gives you the advice on how to approach her. But it only affects one achievement and how you introduce yourself. Everything else afterwards is the same.

(the outfit unlocks some other VIPs like Alyssa Griffin, Cassandra Leigh and Carson Stewart before you meet Winona)