For Chloe, dates should become available through progress, I forget exactly how...
For Amy you need to play as Chloe to progress with her, to take her under 98 shyness; Travis taking Amy on dates to the fair you can further decrease her shyness, and then when she's under 76? shy, you can use Chloe to corrupt her.
Be very careful with using save edit! It can lock you out progression with certain characters ( Chloe and Amy especially ) if you break the cap for certain events to occur ( happened to me, and I had to edit stats and even events in order to progress or/and see content ). I suggest not editing saves until you've finished the content that is cap sensitive...just play normally, or/and stay under the caps indicated in dialogue until you've finished those events. I'm going to start again when the other half of the update drops, because I've missed content...
With the lingerie, I only purchased illegal lingerie and slutty bunny outfits. I was going to leave the other outfits for when they are required to see future content. I did check out the other outfits just by clicking on them. Can't recall anything about any " Right Spot"...Have you tried searching this thread?
EDIT: Onya Crichton...that saves a search.
EDIT 2: Oh if you find you can't play as Chloe, go into save edit and set chloe_play to 1. , and you have to do this everytime you begin a school week, restart game, play as Chloe, progress with Amy, and Detention ( go into male toilets pantiless ), over and again until you've gone through the progress/content...it's a pita to be sure, which is why it's wise not to edit saves before you know what you're doing, and progressed through the caps. Which is why I'm starting again next update...