Lol this is literally years later but I just remembered I had this account and read through all of my old scenarios. I hope this is okay ('∀') please enjoy!
Masaomi: How about we go do something fun, hm? Just the two of us. *insert close-eyed smile*
Ukyo: *he's a little embarrassed, but he thinks its just because he likes you so much* Hey, um.. Are you free anytime soon?
Kaname: I want to take you out, kitten. Have the time of our lives together. What do you say? *stretches out hand to you and smirks*
Hikaru: Have you seen any new boutiques lately? Lets go window shopping! We haven't left the house in a while...
Tsubaki: Ne, (Y/N)-Chan! Let's go on a picnic! The sakuras have blossomed and I've heard its really romantic. *winks*
Azusa: *he sends you a text saying to dress up nice and meet him outside. When you do, he's standing there in a tux with a single rose. He clears his throat* Thought you'd like to go out to dinner?
Natsume: Oi, let's hang out. I- I miss being with you... *clears throat* Are you up for watching a movie?
Louis: (Y/N)-Chan, let's do something that interests you. *Caresses cheek* I want to make you happy.
Subaru: You wanted to learn how to play basketball, right? Well, I thought- maybe I could teach you.. today.. if you want... *trying not to be embarrassed but failing miserably*
Iori: *has extravagant date planned out for you* I hope this is okay... I want you to know how much I love you.
Yusuke: Oi! Let's study together. And... maybe get some dessert after... But only if you want to!
Fuuto: *smirks* You've greatly interested me. I want to take you out. But I will be disguised, obviously.
Wataru://
Sorry if these scenarios are a little off, its been a long ass while.