Requests are still open btw! Hope you enjoy!
Update: Thanks to SkullChick15 who informed me that Morton was missing.

Ludwig

A hill with a starry night sky

Roy

A secret night club that only rich people can get into

Iggy

A popular science museum. He knows a lot about a lot of stuff, and he shares his knowledge with you.

Wendy

To all of your true Wendy fans, you'd know she enjoys ice skating. So you both ice skate together. She kind of had to help you because you were a little clumsy;)

Morton

A beautiful park with an even more beautiful fountain. He has picked some wild flowers from here before hand and put them in your hair as an accessory when you arrived. They were you favorites, [fav flower].

Bowser Jr.

Bowser Jr. surprised with a claming picnic in a park. There weren't many people that day so you goofed around and played [fav outdoor game] together.

Larry

You 2 had a fun but  exhausting day at [fav water park].

Lemmy

You 2 had a fun but exhausting day at [fav amusement park]. You ate tons of food and you won each other a ton of stuffed animals and prizes.

Thank you for reading and I hope you enjoyed! Requests are still open for scenarios as well!