Stephen Colbert’s Awkward First Encounter with Evelyn McGee Turned Into the Love Story of a Lifetime

When Stephen Colbert, the sharp-witted host of The Late Show, tells a story, he knows how to land a punchline. But one of his favorite stories isn’t about politics, satire, or late-night TV rivalries. It’s about the night he almost blew his chance with the woman who would become his wife — Evelyn McGee-Colbert.

It’s a story filled with nerves, comedy, and the kind of fate-driven twist that belongs in a Hollywood rom-com. And yes, it all started with Stephen embarrassing himself in front of her parents.

The Cringe-Worthy Beginning

The year was 1990. Stephen Colbert was 26 years old, still an unknown aspiring comedian, and living in Charleston, South Carolina. He wasn’t yet the cultural figure we know today — no Emmy awards, no political parodies, no monologues skewering presidents. He was just a young man, hopeful, broke, and still finding his comedic voice.

On that fateful evening, he attended a performance of Hydrogen Jukebox, a Philip Glass–Allen Ginsberg collaboration that brought together avant-garde music and beat poetry. In the theater lobby, under the golden lights and chatter of the crowd, Colbert spotted her: Evelyn McGee.

Tall, poised, elegant — Evelyn was standing with her parents. Colbert later recalled that it was one of those lightning-strike moments. He knew immediately he had to speak to her.

And so, heart pounding, nerves jangling, he did the unthinkable. He walked straight up to her — with her parents right there — and blurted out a request for her phone number.

It was bold. It was awkward. It was very Stephen Colbert.

No Number, Just a Scrap of Paper

The moment didn’t go as planned. Evelyn didn’t hand over her number. Instead, she gave him a polite smile and explained that she had another commitment.

Colbert, mortified, scribbled his own number on a scrap of paper and handed it over before retreating.

“I thought I’d blown it,” Colbert admitted years later on The Late Show, his grin masking the lingering embarrassment. “I figured I’d made a complete fool of myself — in front of her, and her parents.”

But as it turned out, fate wasn’t done writing this story.

Her Parents, the Secret Matchmakers

What Colbert didn’t realize at the time was that Evelyn’s parents had noticed him, too. They saw something in the nervous young man who had dared to approach their daughter. Something genuine, earnest, and worth encouraging.

Days later, Evelyn called him. That call — prompted in part by her parents nudging her to give him a chance — led to their first date at a low-key dive bar. Cheap drinks, quiet conversation, and a spark that neither of them could ignore turned what started as an awkward stumble into a storybook beginning.

Looking back, Colbert has often credited Evelyn’s parents with saving his romantic misstep. “I owe them everything,” he once said. “They’re the reason I didn’t crash and burn that night.”

Falling in Love, Against the Odds

From that dive bar date, their relationship deepened quickly. Evelyn matched Colbert wit for wit, joke for joke, but also brought something deeper: stability, strength, and a sense of grounding that complemented his comedic energy.

But love wasn’t without its challenges. Colbert soon moved to Chicago to chase his comedy dreams, while Evelyn remained in South Carolina. Long-distance relationships are tough under any circumstances, but this one was particularly daunting — he was a struggling comic with no guarantee of success, and she was building her own career as an actress and producer.

Yet, somehow, they made it work. Phone calls, shared letters, and trips back and forth kept their connection alive. Their shared Southern roots and love of theater provided common ground, and their bond only grew stronger.

The Wedding and Family Life

In 1993, just three years after that awkward lobby encounter, Stephen Colbert and Evelyn McGee were married. They settled into married life with the kind of balance that many couples envy.

Together, they raised three children: Madeleine, Peter, and John. They built a home in Montclair, New Jersey, away from Hollywood’s bright lights and pressures, allowing their children to grow up with a sense of normalcy.

Evelyn, though an actress in her own right, has often stayed out of the spotlight, focusing on family and occasionally appearing alongside Stephen in playful cameos — most memorably on The Colbert Report. Her quiet presence, however, is central to Colbert’s life.

He has described her as his “anchor,” the person who grounds his larger-than-life persona. “She makes me laugh harder than I make anyone else laugh,” Colbert once confessed, his eyes sparkling with affection.

A Partnership Built on Humor and Strength

More than three decades later, Stephen and Evelyn’s marriage has outlasted Hollywood trends, career pressures, and the chaos of fame.

Colbert has said that he still marvels at how close he came to missing out on their love story. Had Evelyn not called, had her parents not encouraged her, the comedian might have gone on with his life never knowing the love that would define him.

Their marriage, in many ways, is a masterclass in balance. Evelyn’s calm strength tempers Stephen’s comedic chaos. Her private, steady nature allows him to thrive in public. And his wit and humor keep their relationship filled with laughter.

The Charleston Lobby That Changed Everything

Looking back, Colbert often jokes about that first meeting in Charleston. To him, it’s proof that even the most cringe-worthy moments can become the foundation of something extraordinary.

That theater lobby — where he stammered nervously in front of Evelyn’s parents — became the unlikely launchpad for a marriage that has lasted more than thirty years.

Today, Colbert tells the story with a wink and a laugh, always quick to thank his in-laws. “I’m still thanking them for not letting me crash and burn,” he quips.

Why This Love Story Resonates

In an industry where celebrity relationships often burn out under the pressure of fame, Stephen and Evelyn’s story stands out. It isn’t glamorous. It isn’t perfect. But it’s real — rooted in awkward beginnings, tested by distance, and sustained by humor and trust.

Colbert’s career may put him in the spotlight, but Evelyn remains the steady figure behind the scenes, the partner who gives him the confidence to stand in front of millions.

Their story is a reminder that love doesn’t always start with smooth lines or perfect timing. Sometimes it starts with embarrassment, a scrap of paper, and parents who see something you don’t.

The Power of Awkward Courage

Stephen Colbert’s love story with Evelyn McGee-Colbert could have been a missed connection — an awkward lobby exchange quickly forgotten. Instead, it became the defining romance of his life.

What began with a blush and a fumble turned into three decades of partnership, family, and unwavering support. And Colbert himself will be the first to say it: none of it would have happened without her parents, who turned his awkward courage into a lifelong love story.

It’s proof that sometimes, the most embarrassing moments are the ones worth remembering — because they can change everything.