When you think of high school relationships, what comes to mind? Perhaps, a teenage couple with one football jock and one popular cheerleader? While most people experience the same rapid surge of hormones during their teenage years, dating at Webb is drastically different from what one typically sees in cliché high school movies.   

As Webb returns to in-person learning, students also resume socializing in full-force, rekindling the somewhat dormant dating culture during the pandemic. This dramatic rebound may stem from the severe deprivation of face-to-face interactions during quarantine. 

“COVID took away our in-person experience,” Kalman Dong (22’) said. “And now, coming back, people are just excited.” 

Even without the effects of the pandemic on socialization, the dating experience at Webb is still  different from the myriad of other schools in the Claremont area. Given that Webb is a private boarding school, students are around their peers considerably more than they would be at a traditional public high school. At the same time, students are also not fully independent as they might be at a college or university. Therefore, at Webb, students are more intimately involved in each other’s lives, but at the same time, also have a limited amount of freedom under the high school environment. 

“The drama is magnified by the fact that there are so few people at Webb,” Mirabel Raphael (‘24) said. “The social dynamic at Webb is structured around a few groups that interact with each other in a very proscribed way, and the social dynamics definitely contribute to the dating dynamics.” 

Dating at Webb can induce a lot of pressure, because many feel obliged to remain with their partner for the rest of their Webb career. The small student population makes it impossible to avoid someone, so one must be mentally prepared for the consequences and potential awkwardness if things go south.  

“With Webb being so small, and with everyone so involved in each other’s lives, once you become so publicly attached to a person it’s difficult to detach yourself from that person in the minds of others… it can really affect how people view you,” Mirabel said. 

As many students at Webb know, it can be extremely difficult to keep the secrets of the relationship away from their friends, peers, or even their teachers and other Webb faculty in their lives. This lack of privacy caused many students to feel uncomfortable and distressed at Webb. 

“Drama like that spreads a lot faster at Webb because it’s such a small school…it’s difficult to keep your love life private,” Marina Saeger (‘23) said.  

However, compared to the social interactions that Webb normally experiences, the 2020-2021 online school year heavily altered students’ communication with each other. The sophomore class was affected by the lockdown last year more than any other class at Webb, as they entered high school amid a pandemic and did not have the same opportunity to make valuable social connections. 

“It’s mostly the sophomore class that never had any time with each other in person,” said Mirabel. “The segregated school structure also means that people will not get to know each other [unless they interact outside of class] until junior or senior year.” 

Of course, the pandemic had a non-trivial impact on dating culture. Many challenges surfaced as some attempted online dating during quarantine. For instance, people from different time zones and different grades had a tough time connecting with each other. However, others were comfortable with this method of communication, as it is a convenient and less nerve-racking way to meet new people.  

“We can take full advantage of it because you can connect with people even if you are not together physically,” said Naomi Kang (‘24). “For me, it was an advantage, because if I didn’t meet my significant other online, then I wouldn’t have had a chance to meet him at school, on campus.” 

It is not difficult to see how the sudden change in environment motivated students to eagerly jump into relationships when they finally had the opportunity to meet in person.  

Aside from the pandemic factor, another reason why people tend to date in the fall and winter seasons is because during the holiday season, students wish to share the “holiday feeling” with someone. In fact, this phenomenon is so prevalent that it is coined a special term, “cuffing season”. 

Like in many other high schools, the annual fall homecoming plays a crucial role in shaping Webb’s dating culture. A surge of couples arises during this time because people are excited to go to a dance with the person they like or see homecoming as the perfect opportunity to ask someone out. The poster tradition, which is often posted on the student government Instagram page, also adds a layer of glamor to this event and forges a special bond between two individuals. Contrary to other schools, the small student population at Webb almost guarantees that almost every couple going to homecoming becomes public knowledge. In fact, at least five known couples were formed the week before Homecoming.  

Another issue specific to Webb that many other schools do not face is the dating dynamic between day and boarding students. 

Boarding students are confined under various restrictions, including dorm check-ins at night and having to take passes on the weekend, which can present some challenges to their relationship with a day student. They are also not allowed to keep cars, meaning they have limited options to privately spend time with their partner.  

Meanwhile, boarding students also have a unique experience that many other teenagers do not have when it comes to dating, since most typical high schoolers still live at home. Boarding students must learn to independently achieve a balance between academic, personal, and dating life.  

“When I first started dating, my friend felt like I wasn’t listening to her,” Joy Li (‘24) said. “We had conversations about how we should balance time with friend and time with boyfriend.” 

Additionally, due to the uniqueness of Webb’s environment, two boarders might not have the privacy they need when dating. 

“[Boarders] have little to no privacy to their dating lives since they have to fill out passes …it’s more noticeable since they live on campus,” Marina Saeger (‘23) said.  

They might also be hanging out together all the time, a phenomenon that may well blur the boundaries between learning space and personal life and become bothersome for other individuals. 

As for relationships between upper and lower classmen, there exist many stereotypical preconceptions.  

“I think in any school, people usually look down on the older one…[question]why do they need to go after someone younger than them,” Marina said.  

She also points out the large maturity gap between grades, which brings us to our next point. Upperclassmen are busier, so their concerns would be considerably different from their underclassman partner, which could cause problems in their relationship.  

However, there are undoubtedly many positive aspects to this type of relationship.  

“I would encourage him [my boyfriend] to participate in school activities and apply for leadership positions because I experienced that as a freshman,” Joy said.  

We also looked at the general motives of dating within the Webb community. 

“For underclassmen, when they enter high school, they immediately want to find their high school sweetheart,” Marina said. “That’s why they tend to rush into relationships.”  

Upon entering high school, freshmen find themselves meeting a flurry of new peers. So, it makes sense for them to quickly settle into a relationship; establishing themselves in a glamorous and exciting social circle gives freshmen a sense of belonging and helps them adjust to the seemingly intimidating high school life.  

In comparison, upperclassmen have been a part of Webb for longer, so their experience would teach them to not impulsively start a relationship. Perhaps this means that they are more likely to date due to genuine attractions.  

In the end, when we look at the network of relationships at Webb, how does this experience contribute to our growth as teenagers and high school students?  

While the uniqueness of Webb’s environment does present some challenges and nuances to dating, it can also be one of the most valuable memories of our high school experience. It is important to establish boundaries of interactions and maintain a balance between academic and personal life. Each individual can determine the balance that is right for them, taking into consideration the social dynamics they are involved in, and what environment they live in.  

At the end of the day, we need to keep in mind that during our time at Webb, our actions are important as our individual experiences affect not only ourselves, but our entire community.