Jayson & Jackson

1.16.2026 • St. Louis, MO
238 Days To Go!

Jayson & Jackson

1.16.2026 • St. Louis, MO
238 Days To Go!

The First Message

Jayson and Jackson met in the summer of 2019 while interning in Washington, DC. Jackson messaged Jayson saying, “Hi, I’m Jackson, a theater major at SLU.” Though they were living in the same housing in Fairfax, VA, they discovered they lived just a mile apart in St. Louis and had mutual friends. After a few hours of texting about theater and shared connections, Jackson invited Jayson into the city to visit the Folger Shakespeare Library.

The First Date

Jayson immediately thought, “Wow, he’s so cute” when he saw Jackson in person for the first time. They quickly got into Jayson’s car and headed to the train station. The train ride was full of easy conversation, including a mutual love for public transportation and urban planning. After getting off at McPherson Square, near the White House, Jayson suggested they stop for coffee at Compass Coffee, where Jackson learned about Jayson’s barista passion—and his surprise that Jackson didn’t drink coffee.

Jayson then proposed a 2.5-mile walk instead of hopping back on the train. As they walked, they stumbled upon Ford’s Theatre and spontaneously decided to tour it. Afterward, they visited the Folger Library, which wasn’t what either expected but still interesting. Their adventure continued with a stop in a park to chat, and then a last-minute decision to head to the Kennedy Center for a free concert.

Their First Show

At the Kennedy Center, they discovered "Hello, Dolly!" was playing that night with student rush tickets. They bought tickets and ended up seeing their first show together—something that became a favorite date activity.

The First Cuddle

After the show, they took the train home, where Jackson snuggled up to Jayson. It was a quiet, comfortable ride, and when they got home, they shared a warm hug and said goodnight.

The First Few Months

They continued dating after leaving DC, seeing a play at the Shakespeare Theatre Company and hanging out with friends. Even after they went back to school, they kept in touch and reunited a few weeks later. As they spent more time together, they realized just how much fun they had and how much they enjoyed each other’s company.

The First Time Someone Said It

Weeks later, Jackson invited Jayson to Chicago for fall break—their first vacation together. At that point, it was clear their relationship was more than just friendship, but neither had used the word "boyfriend." One night at a bar, Jackson texted friends about his “boyfriend” staying with him, showed Jayson the message, and asked, “Is this okay?” Jayson smiled and said, “Yes, it is.”

The First "I Love You"

For Jayson’s 22nd birthday, he visited Houston with his childhood friend Shilo. While out at a club, Jayson dropped hints he wanted to tell Jackson something important. After stepping outside to call him, he got Jackson to say “I love you” first.

The First Couple of Years

Over the next few years, Jayson and Jackson traveled, saw countless shows, and continued to grow their relationship. Their bond only deepened, filled with spontaneous adventures and shared memories.