On the first day of Tiger Takeoff in 2022, Gemma Prince, senior psychology major, approached someone who she thought was her third-grade best friend. In reality, she met Jake Cipolla, senior music and education double-major. Four years after this mix-up, the two are roommates and best friends.
The connection wasn’t instantaneous; the pair said it was gradual. As their first semester at Trinity played out, they became involved with the Trinity University Players (TUPS) and gradually spent more time together through hangouts organized by a mutual friend. Cipolla was the first to suggest deepening their friendship by arranging a group and making a day out of visiting the Japanese Tea Garden.
Prince and Cipolla bonded over music in particular; Cipolla was in the chamber choir while Prince was in the Trinity Choir. Along with seeing each other in TUPS and choir practice, they also spent time in the practice rooms singing together and learned they enjoyed each other’s company.
Their friendship evolved, and they moved in together in August 2025. What initially began as a running bit that started in their first year — that they might one day move in together — recently became a reality when Cipolla’s parents bought a house in San Antonio that they use as a rental property.
Moving in together never complicated their friendship, despite being different genders. According to them, gender norms did not factor into their friendship.
“I’m gay, so that also takes into effect,” Cipolla said. “There’s the generalized stereotype of guy-girl friends. One of them likes the other one, but doesn’t say anything, and ruins the friendship. But that’s not an issue because we have very different types, and, well, we’re both into men.”
According to Cipolla, the key to a lasting friendship is maintaining contact and finding comfort in each other’s space. He said that it helps to reach out and extend the invitation to a friend if they want to hang out.
“I’ve had situations where, yes, I did try and reach out to somebody, and they’re really flaky,” Cipolla said. “So at some point you just realize some people don’t want to initiate hangouts for one reason or another. You just have to move on.”
Similarly, Prince said that learning what each friend needs is important. According to her, being attentive is important when learning how to be friends.
“Jake will ask me if I’m having a really bad day or something,” Prince said. “He will be like, ‘Okay, do you want advice, or do you want me to just listen?’ And that makes a huge impact.”
With every pair of soulmates come issues, though. Prince and Cipolla realized that, as with every close friendship, communication goes a long way toward mitigating potential complications. Although they have had occasional disagreements, they have both made time and effort to address and talk things out.
“If there’s really something, either determine if it’s something you can get over, and if it’s something you can get over, fine, move on,” Cipolla said. “If it isn’t and actually is an issue, just take them aside. Chats take like five minutes, 30 seconds. If it’s really that big of a deal, and also in the case that it is drawn out of proportion, you shouldn’t be friends with them if they’re not willing to respect [you].”
Every besties’ story has a unique beginning. Cipolla and Prince’s highlight how a small misunderstanding sparked a lasting connection. They are both set to graduate in May 2026 and hope to keep in touch after graduation.
