How one couple’s love story led them back to a New Trier classroom

When Alan Cosby and Theo Jordan made their first real estate transaction in 2023, they didn’t know it would be the best deal of their lives. 

The two, now both realtors, first met as high school freshmen in their joint eighth/ninth period English-history class in 2001, when they were inaugural members of New Trier’s Northfield campus.

“Everything was very new and scary,” Jordan told The Record North Shore. “I was in this big class, and I hated reading out loud, but there was this one kid in the class who was very good at reading out loud and pretty funny and cute, and that was Alan, and I had kind of a crush on him. But then, after that, we never really spoke again because the class size was so big, and we had different groups of friends.”

While the two would say “hi” to each other in passing in the hallway, their interactions essentially stopped there. (Although, when asked if they had crushes on each other then, Jordan playfully asked Cosby, “I did. Will you admit that you did?” He laughed before admitting, “We noticed each other.”)

The two reunited in 2023 when Cosby’s clients were looking to buy a condo in Wicker Park, which happened to be listed off-market by Jordan and a co-agent. Cosby’s clients loved the property and put in their offer. 

“We had a pretty smooth transaction overall,” Cosby said.

Indeed they did — and not only when it came to the condo.

During the showing, Cosby told Jordan he’d be having his birthday party in a couple weeks and promised to invite her. True to his word, he sent her the invite shortly thereafter, and Jordan attended the bash. From there, it was “off to the races,” Jordan shared. 

Making it happen

For their first date, they went out to The Warbler in Lincoln Square and then watched a couple of episodes of Netflix’s “Love is Blind” and, Cosby said, “just never stopped.”

To propose on July 27, Cosby thought up a ruse to get Jordan unsuspectingly back to New Trier’s Northfield campus. He enlisted in the help of Mr. Hayes, the couple’s freshman year English-history teacher, who was there when it all started and was luckily still teaching at the high school.

According to Cosby and Jordan, Hayes went out of his way to make the proposal a success, helping make sure the couple could get onto the campus, which was under construction, on a Saturday. 

First, Cosby told Jordan they’d be visiting his mom in Glenview, stopping at Three Tarts Bakery in Northfield to pick up some sweet treats. As they drove past the Northfield campus, Jordan said she “fell right for” Cosby’s plans, saying, unprompted, something along the lines of, “Oh, it’s so funny, we haven’t really driven by here, but this is where it all started.”

To his relief, Cosby was able to easily get Jordan out of the car and onto the campus, suggesting they take a picture where it all began.

As they walked the vacant campus, Hayes strolled out of the building toward them.

“All of a sudden, this man came out of the school and I was like, ‘Oh no, we’re going to get in trouble. We’re not supposed to be here,’” Jordan explained. “And then all of a sudden Alan was like, ‘Hi Mr. Hayes,’ and I was like, ‘Holy —! What are the odds? This is going to be a wild story for your mom.’”

Cosby asked Hayes, in on the act, if the couple (with Jordan still unsuspecting and excited to catch up with her former teacher) could see their old classroom for a picture. 

Upon unlocking the classroom door, Hayes left the couple alone, and Jordan beelined for her old desk, missing the display of roses, class yearbook and old golf uniform (they had both been on the golf team freshman year) in the center of the room, until Cosby suggested Jordan turn her attention toward the mementos. 

In the yearbook, which Cosby had not originally signed for Jordan when they were schoolmates, he had written his proposal. 

When Jordan finished reading it, she saw that he was down on one knee.

Wedding bells

After the big moment and a resounding “yes” from Jordan, the rest of the day was filled with a mani-pedi surprise for Jordan, six dresses for her to choose from (all loaned from her favorite shop and arranged by Cosby) and a “16-person family dinner” that was really a 100-person surprise party. 

The couple plans to get married on May 4, 2025, in Charleston, South Carolina.

On whether Hayes might be in attendance for the big day, the couple, grateful for all his help, said they’ll definitely be sending him an invitation, but they know it’s a big ask and don’t expect him to travel to South Carolina on a school night. 

“You never know who you are going to meet in high school,” Cosby said.

Jordan added, “Yeah, you never know who you are going to meet and then reconnect with all these years later.”

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