It was 3am on a January morning, and Bobby Lundquist (College ’16) was freezing. He was almost at the end of his rounds: The nightly walk around the Quad—a standard part of his Resident Advisor (RA) duties. Suddenly, beyond the snow–lined stone buildings and shadowed statues, he stumbled upon what his training sessions would have label as a “drug–related incident”: a group of students who were most likely high.

Bobby asked for their Penn IDs, normal RA procedure. The students refused and panicked. Within minutes, one began sprinting through the Quad. Bobby took off running after him.

“A high–speed chase in the quad at 3:30 in the morning wasn’t something that I had signed up for,” says Bobby, now in his second year as an RA for Fisher Hassenfeld College House.

Though RA policies are strict, most don’t address the gray area situations advisors find themselves in, including late–night drug–runs. While maneuvering through a dual–role as friends and supervisors, RAs often rely more on personal assessments and spur–of–the–moment judgments than university policy to navigate their halls.

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There are currently 82 undergraduate RAs and 121 Graduate Advisors (GAs) employed by Penn Residential Services. It’s a competitive process, and students are expected to meet a GPA minimum and submit both personal and academic recommendations to be considered. Still, not much can truly prepare a student to oversee their younger peers.

An RA/GA is typically in charge of twenty to 30 residents every semester. Training is about a week and a half long and includes modules on student activity reporting requirements, sexual and partner violence, cultural sensitivity and mental health.

Penn’s guidelines for RA/GA and resident relationships are far from concrete. Though the RA contract requires applicants, if chosen, to “refrain from engaging in any exploitative relationship with a resident within their area of direct supervision,” the definition is relatively ambiguous, especially when RA/GAs are encouraged to form close bonds with students living in their halls.

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Bobby hosts a kickback every Sunday night, called “Bread and Jamz,” where his residents and other upperclassmen can come and mingle. He bakes fresh bread and cinnamon rolls, which people enjoy while listening to music. It’s creative and casual—what Bobby calls “an alternative social environment,” which he advertises on Facebook.

Social media can provide RA/GAs with tools to interact with residents in a sphere beyond university policy. A recent research analysis published by the College Studies Journal explained that “RAs reported that they had seen references to issues such as depression, problem drinking, homesickness and academic problems on the Facebook pages of their residents.” Furthermore, “RAs described using Facebook to identify not just whether or not residents display depression or problem drinking…. RAs also discussed how Facebook can be a unique way to gain insight into a resident who is not comfortable or able to discuss his or her concerns in offline settings. “

Still, there are boundaries. One anonymous student commented that RAs and GAs are strongly discouraged from posting about personal residence matters online.

The lines are certainly blurred offline too.

Jesse Ellingworth (Wharton and College ’16), a returning RA in Rodin, is a brother at Phi Kappa Psi, which creates awkward tension when he runs into his mostly–freshman residents at off–campus fraternity events.

“If I see my residents at one of my parties, I think that’s great, it’s fun,” he laughs. “But if they’re in a severe situation, if they really needed help, it’s not even an RA thing, it’s a human thing [to help].”

But outside the jurisdiction of the university, it’s his decision whether or not to follow protocol.

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Ramón Garcia Gomez (College ’18) lived in Hill his freshman year and quickly became close friends with his GA. As a freshman from California, the move to the East Coast was somewhat difficult.

“For Thanksgiving, I couldn’t go back home,” Ramón describes. “So my GA took me and a bunch of other people out to this fancy dinner on Thanksgiving. It showed that he obviously cared about us.”

Bonding can also manifest in more casual settings.“I was doing homework in the lounge, and he walks in and brings all this Chinese food… it was $200 worth of Chinese food. I didn’t know how to use the chopsticks, so he was feeding me these dumplings, telling me to suck on them first, ’cause that’s how you ate them. Then someone walks in and sees him feeding me, telling me: ‘Suck on them, Ramón!’”

Ramón’s now working with his former GA on his startup: launching an app called Link. “He emailed me over the summer and was like, ‘Hey, do you want to be part of this app?’ So I said sure.” He implies that it was a natural occurrence considering how close they were.

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RAs and GAs have to be careful not to cultivate “special priority” relationships. It can be a problem when an RA has a best friend on their floor, potentially demonstrating favoritism.

Carissa Gilbert (College ’15), an RA from Kings Court English House for the past two years, laughs, “Everyone always thinks that they're the favorite, and I reassure them that they are.”

Though she has no particular favorites, one resident stand outs.

“From my first year of being an RA, Shorya Mantry… I've kind of made [him] into a hall mascot,” she says. “We gave him a shoutout in 34th Street and put his face on the back of a fling tank. Whenever I travel I always wear that tank so people all over the world can see his face. It's kind of weird, but it works.”

But sometimes, it’s the residents who make their RAs feel welcome.

Bobby describes how it can be a pleasant surprise to have the residents do something special for them. “Whenever the resident does even the tiniest thing, it completely turns your day around.”

And the freshmen on his hall can help celebrate the most important days.

“Last year one of my residents knocked on my door. It was my birthday; I was in bed and about to go to sleep when someone said there was a mouse in their room. I came in and my whole floor’s in there with cakes and candles, and they’re singing me happy birthday.”

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When it comes to RA romantic relationships, it’s widely understood that hall residents are off–limits. But the reality doesn’t always adhere to protocol.

As an RA supervising a freshman hall, Bobby’s aware of the moral boundary drawn at romantic relationships.

“You can create a power dynamic that wouldn’t lead to a healthy relationship,” he says. “If an RA or GA is doing a good job, they’re fostering a relationship that’s built on trust… With a romantic relationship, if it didn’t go well at a certain point, it would create an unsafe space for the resident.” The RA/GA is meant to embody a safe space for the resident; if that safe space is compromised or even removed, it can be difficult for a resident to seek the support they need.

Jesse acknowledges that sexual or romantic relationships aren’t typically permitted.

“The meaning behind that,” he explains, “is so that no other resident gets neglected. That’s your duty: To make sure everyone’s receiving the same support.” Jesse admits that matters like these must be judged on a case–by–case basis; the rules exist because, “the line needs to be drawn so it doesn’t happen all the time.”

It’s a gray area that he highlights needs to be discussed with the House Dean. If a romantic relationship were to occur with a resident on the same floor, the House Dean must notified and approval is needed.

Tommy Murphy, Rodin’s House Dean, admits that chemistry naturally develops with certain people more so than others. “There are times when the RA or GA will connect with certain residents more because they have things in common or enjoy hanging out with them more.”

Murphy is adamant about crafting an accepting environment for residents and RAs/GAs alike so the RA/GA can feel comfortable enough to disclose an intimate relationship. Dating and hookups are fine as long as it doesn’t undermine the RA or GA’s professional role in regards to their residents: “I would hope that there’s enough respect between them and their partner that they would never take advantage of that role.”

In a romantic relationship, the RA/GA and the resident face unique issues that are partly engendered by the power dynamics of job position, gender and age.

Although she’s not interested in pursuing anything with her residents, Alix Desch, a Rodin GA, is aware that it happens. She describes how female RAs/GAs will face the customary stigma of disparaging labels (being called “slut” or “easy”), whereas male RAs/GAs face criticism for taking advantage of their position of power. Though gender–based criticisms are nothing new, they can be brought to the forefront of discussions pertaining to relationship power dynamics.

She recounts one incident at Penn that ultimately involved police. A male GA had been sexually involved with as many as six female students—all of whom lived on his hall. This resulted in a physical altercation between two roommates who found out they were both side–women to the same man. Instead of confronting the male GA, the roommates took out their anger on each other. Alix remarks that, “It’s likely that there wouldn’t have been paperwork involved if not for the physical fight and involvement of the police.”

Of course, Alix’s story is an extreme example of unethical RA/GA behavior; most RAs and GAs are highly qualified for their jobs considering the lengthy process they go through: interviews, a letter of application, resumés and letters of recommendations. Moreover, each semester, an RA/GA is evaluated on their performance based on their successful completion of assigned responsibilities.

But sometimes, the RA judgment results in disparity.

One anonymous student commented, “While many of my friends bragged about taking shots with their RAs on weekdays, my hall supervisor sent me to the House Dean for drinking wine and listening to Taylor Swift with my friends on a Thursday night.”

Ultimately, no policy can fully address the challenges and joys that being an RA can bring. It’s tricky to integrate professionalism with friendship and even harder to codify the balance. Ultimately, the relationships maintained between RAs, GAs and their residents are fluid and cannot be prescribed by University policy.

“It’s a ridiculous job,” Bobby concludes. “But it’s really rewarding too. All the small moments end up feeling really big.”

Amanda Reid is a sophomore in the College from Vietnam. She is a staff writer for Street.