Evangeline Grossman (‘85), known as “Van,” in her days at Webb, entered the school her freshman year from Foothill Country Day School, and became heavily involved in varsity tennis. At first, she was intimidated by the large ratio of boys to girls, especially in social settings like finding a seat at the dining hall.  

At that time, the Old School House was a campus hub for VWS. Most surrounding classrooms were for VWS classes and there were lockers for VWS students to store school supplies. The faculty lounge used to be a small student center for VWS students to hang out between classes and change before sports.   

Grossman believed that the pioneer class helped set up Webb by small actions such as integrating with WSC and doing well academically, to make it possible for the school to expand and keep taking on new female students.  

She formed deep bonds with the VWS pioneer classes; leaving Webb was especially hard as many of her classmates were individuals with whom she shared not only the Webb pioneer experience , but also her elementary and middle school years at Foothill Country Day School. The connections she made at Webb helped her obtain her first job at a law firm, which greatly propelled her to where she is today.  

In conversation about the VWS and WSC dynamic, we found dating culture in the pioneer years to be intriguing. Dating was one of the ways VWS and WSC connected and integrated. “I don’t think now it’s the case, but pretty much everyone had a boyfriend,” Ms. Grossman (‘85) said. “That was sort of the way you integrated with guys because they all had friends, so you got to know a lot of the guys really well.”