The smell of Axe body spray, sweaty socks, and cheese puffs permeates the room as eight teenage boys cram into the hotel at a high school journalism conference, toppling over each other to catch a peek at the text on the tiny Blackberry screen: “Meet me at the vending machines.” The room erupts in screams and high-fives as 17-year-old Lenny Goldman makes his way past the quirky journalism teacher’s room, sneaking out to meet 16-year-old Ali (now known as Alexandra) Fields.

This high school mischief sparked a more-than-20-year relationship between Mr. Goldman, Latin’s current 9th and 10th Grade Dean of Students, and Ms. Fields, Latin’s Director of College Counseling.

Before this vending-machine escapade, a clan of 10-15 students representing Stevenson High School—half newspaper staff and half on yearbook—boarded a flight to San Francisco, awaiting an exciting weekend at the Journalism Education Association (JEA) and National Scholastic Press Association (NSPA) journalism convention. Yearbook editor and sophomore Ali had just boarded the bus when a Stevenson High School newspaper editor she had never (to her knowledge) met before offered to carry her bag. His charm only grew the more time she spent with him.

“I would say Mr. Goldman and I were pretty drawn to each other quickly, and something I remember distinctly is that he was so funny,” Ms. Fields said. “He was just widely funny, I was like, this is the funniest guy I have ever met.”

After their first interaction, their connection quickly blossomed, and just over a week later, on the way to their friends’ bonfire, Mr. Goldman asked Ms. Fields to be his girlfriend. Despite their young age, Ali had a gut feeling about this relationship: She knew it could be something more than a cliche high school romance.

“When I got home from the journalism convention, I told my mom, ‘Mom, I met this boy, and I think he’s going to be my boyfriend,’” Ms Fields said. “She was asking me about him, and I said, ‘I know this is going to sound crazy, but I’m going to marry him.’”

Their instant connection led to a year of dating in high school until Mr. Goldman graduated and went off to college at the University of Missouri, Columbia, and, notwithstanding the distance between them after he departed, the relationship continued.

At first, navigating this change proved tricky, as Mr. Goldman explained. “It was really sad and difficult at first, and we didn’t know how it would play out,” he said.

They managed to make it work, though, and at an even greater distance once Ms. Fields graduated from high school and matriculated to Barnard College. Their time dating in college allowed them to create meaningful experiences with friends and focus on school without the extra clutter of romantic relationship drama.

Although they don’t necessarily recommend going into college with a serious relationship, they believe it actually worked well for them. “I think we both felt it led to an awesome college experience,” Mr. Goldman said.

Despite this positive experience, after Ms. Fields’ senior year of college and Mr. Goldman’s first year post-graduation, they both felt they needed a break to explore life after college without the responsibilities of such a committed relationship.

Although Ms Fields described this break as “really hard,” she recognizes the importance of this period of independence for both of them.

“We had grown so much and were two very different people living independent lives,” she said. “It was important for us that we went out and dated other people and experienced different things and also made a more conscious choice to come back together as adults.”

After about 10 months apart, the two re-evaluated their choices and decided to get back together. The decision to start dating again helped them gain confidence in their relationship, knowing it wasn’t just convenient or situational. Rather, it was a conscious choice to commit to spending the rest of their lives together. Immediately after, they moved in together on 11th Street in New York, living like classic New Yorkers in a tiny one-bedroom apartment without a toilet.

Ms. Fields described one particularly Ross Geller-ish experience. “I’ll never forget when one day Mr Goldman left for work earlier than me, and I went out to go to the bathroom in the morning in my pajamas, and the door closed in on me,” she said. “I got locked out and had to knock on the neighbor’s door, get let into their apartment, climb out the fire escape, and climb through the window of our apartment.”

This proximity, though, helped them bond, and after four years living together in New York, Mr. Goldman decided it was time to propose. So, when the two headed to Bermuda for a romantic beach vacation, Mr. Goldman took along his great-grandmother’s ring.

Salt air whipped at their helmets as they cruised down the winding roads of Bermuda, stopping at an overlook where Mr. Goldman decided to propose. He reached down to grab the ring, but, shaky with nerves, the ring slipped out of his hand and started flying down through the air and toward the edge of the cliff.

Miraculously, before she even had time to process what was happening, Ms. Fields caught the ring mid-air, saving it from landing in the ocean. High on sheer terror and adrenaline, Mr. Goldman blurted, “Want to get married?” and the rest was history.

In 2015, the two got married at the Intercontinental Hotel in Chicago. Four years later, they moved back home to Chicago to be with their families and for Ms. Fields to take a position as a college counselor at Latin.

Mr. Goldman pursued his teaching career at other schools in Chicago, and then, around five years ago, he decided to interview at Latin. Although this transition meant the two would work in the same building, they weren’t worried about being too close.

“When he first thought about interviewing to work here, we talked about it, and it was like: I work with the 11th and 12th graders in my role; Mr. Goldman was applying to teach 9th and 10th grade English. I’m on the third floor; he’s on the fifth floor. Our lives would be so separate,” Ms. Fields said.

After discussing how their lives would intersect working in the same building, the couple decided Mr. Goldman should take the position he’d been offered. He spent four years as a 9th and 10th grade English teacher until this year, when he transitioned to the role of the 9th and 10th grade Dean of Students. (He still teaches one English class.)

Now, instead of two floors of separation, their offices are literally two doors down from each other. Although working so close can sometimes blur the line between work and life, the two enjoy understanding each other’s daily schedules and challenges.

The couple also love the type of community that working together has afforded them, especially since having their first child, Desi, in 2022.

“The best part is we take him to Latin events all the time. The big game, or just a random soccer game, or the musical,” Mr. Goldman said. “To have our 3-year-old here with 20 high schoolers who know him by name—and he’s cheering ‘Go Romans’ at home—it’s just a very special sense of community that is really cool to be a part of.”

Not only has having a child helped grow their community, but it has also altered their relationship in ways they never imagined.

“We have officially crossed the threshold where we have been together longer than we have been apart in our lives, so now to have this little combination of us is crazy,” Mr Goldman said. “But it’s really fun because we see totally new and incredible sides of each other come through in parenthood that we certainly didn’t envision when we were 16.”

Upper School history teacher and Student Government Advisor Debbie Linder has worked with both Ms. Fields and Mr. Goldman, watching their relationship blossom as they have transitioned from colleagues to co-parents.

“When I found out that they were married, I was shocked, because they struck me as being so different from one another,” Ms. Linder said. “Now that I have worked with them for several years, I can’t think of them not being together. They are fantastic partners, as parents, as spouses, and as educators. Latin hit the jackpot with this dynamic duo.”