Written by Megan Li
I was swamped the summer before my freshman year at Hillsdale College. Behind the graduation parties and travel plans loomed the packing list for college and forms that needed completing. When I came upon the freshman housing form, I was relieved to find the option of leaving roommate selection up to the College. But when I told my other rising-freshman friends that I had not picked my own roommate, I received horrified looks of confusion. “Why would you do that?” “My cousin’s friend’s sister told me that when she didn’t pick her roommate, she got paired with this total weirdo…” I was starting to regret my decision.
When my roommate’s contact information showed up on the housing portal at last, I stared at her name. This was a complete stranger I would share one room with. What kind of person was she? What if we didn’t get along? What if she didn’t like my habits and quirks?
When the call we had scheduled connected, I saw a girl with bright eyes and an equally nervous expression on her face. “Hi,” she said with a little smile, and something heavy seemed to lift off my chest. Our ensuing conversation was terribly awkward, punctuated by much silence, but I immediately had a good feeling about her. We found that we had almost the same taste in music and books, as well as similar religious beliefs. Our personalities, though different, fit remarkably well together, and by the end of our first semester, I was grateful to call her not only my roommate, but one of my best friends.
So how did this happen, I wondered. How did the College seem to know exactly what I needed in my life—a complete stranger that transformed into someone I now could not do without?
Dean of Women Rebekah Bollen and Director of Field Recruitment Jenny Pridgeon had the answers. Mrs. Bollen explained that when the housing forms come in, the deans’ secretaries divide the students with and without a pre-selected roommate into piles of their preferred residence halls. Those piles are then handed to Mrs. Pridgeon and her team of admissions counselors.
Mrs. Bollen explained that the freshman housing forms supply many of the details the staff needs to put roommates together. The form asks for the student’s rising and sleeping habits, their favored room environment (a social place to hang out or a quiet place for studying), level of preferred cleanliness, music taste, hobbies, how they would describe themselves, and what they look for in a roommate—one of the more important considerations, according to Mrs. Pridgeon.
In early June, the admissions counselors congregate in a room on campus. “We’ll spend a day—we call it Roommate Pairing Day, and it’s one of our favorite days of the entire year,” Mrs. Pridgeon said. “We divvy out all the roommate forms, and then we just start talking. We’ll say, ‘oh, I have someone who’s from California. Is there someone who lives close?’ Because then we think, ‘If a distant person can room with someone who lives nearby, then for the shorter breaks, they can hang out for the weekend,’” Mrs. Pridgeon said, providing an example of the team’s considerations.
If the team finds two students with conflicting sleeping habits, they usually refrain from pairing them, unless there is more to consider. For example, if two students have similar interests in music, books, and hobbies, are looking for a best friend in their roommate, and generally seem to line up well, the team may pair them even if their sleep habits differ.
Though the team prefers to put students in their selected residence halls, there are rare cases that students are placed elsewhere. Usually, it is a result of the team believing the culture of another residence aligns more with the student’s character.
After reviewing the students’ profiles and interview notes from past conversations, the admissions team starts pairing. Then the deans, in partnership with the admissions team, build the hall and suitemates dynamics through consideration of interests and spreading athletes throughout the dorms.
“We’re excited when students entrust this to us,” Mrs. Pridgeon said. “We try to make the best decisions that we can, not that we’re perfect. But I would just encourage students—if they want to request, they totally should, but if they don’t really know anyone, we promise to do the best job that we can.”
Should a roommate pairing encounter conflict, Mrs. Bollen said, “We always use it as an opportunity for learning, to live and grow through conflict.” She explained there must first be open conversation between the two students, and should that not go well, the next step is a mediated conversation.“We try to work with the students to improve their living arrangement through communication and compromise, because that’s actually an incredibly important life skill,” Mrs. Bollen said.
Mrs. Bollen encourages prospective students to take the time to fill out that housing form due to the attention the team pays to it. “There’s also something to be said for being excited about the possible connection-forming in a way that was never expected or with somebody very unlike yourself. More often than not, some of the best roommate matches can be quite different but have some unique things in common,” Mrs. Bollen said.
For me, that one day of roommate pairing has led to the eternal blessing of lifelong friendships. Now, as I sit across the cafeteria table from my freshman year roommate, and beside my freshman year suitemate who became another one of my best friends, I am reminded of Mrs. Pridgeon’s words: “If you don’t expect too much out of it, it might surprise you how much you get.” And what a surprise it has been indeed.
Megan Li, ’27, is a sophomore studying economics and journalism. When she isn’t consuming an unhealthy amount of caffeine to finish her homework, you can find her curled up with a good book, taking photos outdoors, or playing her guitar.
Published in February 2025
