Ponyboy: He had school on the day you were sick. You both of course went to the same school. Darry wouldn't let Pony miss anything though, because you were already missing homework, and other things. But when he got home, he would bring you all your homework, and he stopped at the library and got your favorite book. He also got you some food from the Dingo. And medicine, duh.
Johnny: You got sick because of how cold it got in the lot. It wasn't anything major though. It was only a summer cold. Sometimes in the summer it would feel good to be cold but if your sick. It doesn't help. After that night, you both slept at the Curtis's house.
Sodapop: You were trying to hide that you were sick. Soda didn't seem to notice for awhile anyway. Plus he was really busy, not woke wise, but with Steve. You became jealous a little bit. Later that night the two of you were in bed and you had passed out. Fever. He was horrified and put a damp washcloth on your forehead. Then when you woke up some medicine, and plenty of kisses.
Steve: You were driving and cruising around town. Someone swerved in front of you, making you slam your head harshly on the dashboard of the car. You ended up passing out on the scene. Steve cursed loudly for about five minutes before slamming on the gas pedal and zooming over to the hospital. Turns out you had a minor concussion
Dallas: One too many drinks. Obvious isn't it? But you wanna know who's fault it was? Dally's. Because he was drunk, then you got drunk. He kept daring you and challenging you to drink more. When you woke up you had a massive hangover. You were throwing up. Dally thought you were pregnant at first and starting freaking out. Then you-(the voice of reason) explained to him about last night. I'm surprised you remembered what happened. Then for the first time. He apologized to you. And he spent the whole day with you. No dirty talk or whatever.
Two-Bit: Just like Dally's except with food. You both entered a baking contest, he thought your cakes were the best! And you did win! So congrats! But after, Two-Bit decided it would be a good idea to run around and "taste test" all of the other cakes. Later that night, the whole gang had a barbecue. You ate too much there as well. When you were both going home, you hurled in the alley. Two-Bit picked you up, after you were finished and walked into the pharmacy and got some medicine along some other things.
Darry: You lost your voice. Strep throat. Good thing he took you to the doctor and got some medicine right away or you could've got an infection. But that Darry being Darry! Afterward, he knew you weren't supposed to eat dairy products (😉) but that didn't stop him from buying you ice cream! And you gotta a huge teddy bear!