Tim
She walked along with Gladion, and she looked around, looking for a specific place, and after a little bit, she finally found a... Clothes store? She turned to Gladion and put a hand on her hip, "You need to expand your closet, it's been 5 years and you're STILL wearing that sweater." She ruffled with his hair a little bit. "Even though you do look adorable in it, you at least need some sort of variety!"
Rita
He was confused when they stopped infront of a shop instead of a Restaurant, and he basically zoned out throughout her explanation until she messed with his hair, "H-Hey!" He heard her comment and his face turned red, "A-Adorable!? I.." He frowned and crossed his arms, "I'm not adorable.."
Ann
*Darcy was walking along, enjoying itself. But Darcy noticed what was happening. So Darcy went back to the cliff*
Tim
She grabbed his hand, "Keep telling yourself that~!" She led him into the store, and he just gave in and let her drag him around.