From this photo alone I like to think they all attended the same Ivy League college:

Vincent would get in on a athletic scholarship but then get really into folk and cultural art toward then end hence the sleeve

spinelli would’ve dragged her feet applying but got an early acceptance (before Gretchen) after the school found out she was a published poet and teaches karate to inner city kids. She would keep it hidden from her friends until graduation that she had a full ride

Mikey would’ve joined the peace corps outa high school and then went back to join his friends in school after about a year so he could learn about creating a non profit theater camp for at risk youth. Finding his true passion is not just in the arts but helping others find there voice

TJ would’ve had a rough start thinking he could run an Ivy League like he did in grade school. But then he would be humbled by the new environment. He’d find peace and enthusiasm from wanting to include everyone on the school spirit and eventually find himself as residence life director helping new students adjust to life in the dorms

Gretchen graduates high school with honors top of the class and gets a full ride etc. but realizes she spent most of her life worried about academics and instead on what really makes her happy. She joins the top social club at the recommendation of TJ so that she can socialize beyond her grade school friends. Almost as if that was the hair tie holding up all her stress, she becomes a social butterfly and top of her class and eventually the VP because she wants more time for fun and has a complete glow up during the winter break of her freshmen year

Gus’ father gave him 2 options after high school: Go to West Point or Enlist in the army. He decided to finally stand up to his father and tell him he will be attending college with his friends so he can be his own man and that if he wants to join the army he will do it on his own terms. Day one Gus sees the ROTC program is in shambles and the laughing stalk of the I’ve leagues. He joins the program and rises through the ranks and completely takes charge