RT Stephen Colbert’s Most Awkward Moment Turned Into a Lifelong Love Story He’ll Never Stop Telling

Stephen Colbert’s Most Awkward Moment Turned Into a Lifelong Love Story He’ll Never Stop Telling

A painfully awkward moment when Stephen Colbert failed to get Evelyn McGee’s number in front of her parents unexpectedly turned into a heartwarming love story, proving that even the most embarrassing beginnings can lead to lifelong happiness.

Before Stephen Colbert became the sharp-witted host of The Late Show, he was just a nervous young man trying — and failing — to ask a girl for her number.

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That girl was Evelyn McGee, the woman who would eventually become his wife.

But the story of how they met wasn’t a smooth Hollywood romance — it was an unforgettable comedy of errors that Colbert now recounts with equal parts embarrassment and gratitude.

The moment happened decades ago in Charleston, South Carolina.

Colbert had returned home after a difficult breakup and was still figuring out what to do next.

One evening, he attended a local theater performance — and that’s where fate staged its most unexpected scene.

As Colbert later recalled on his show, he looked across the crowded lobby and saw Evelyn for the first time.

“I just thought, ‘That’s her,’” he said, remembering the spark that hit him instantly.

Gathering what courage he could muster, Colbert approached Evelyn.

What he didn’t realize at that moment was that her parents were standing right beside her.

Trying to strike up a conversation, he stumbled through introductions before blurting out, “Hi, I’m Stephen.

Do you—uh—come here often?” The words barely left his mouth before he realized how painfully awkward it sounded.

Evelyn’s parents exchanged amused glances, while Colbert turned beet red, fumbling for an exit.

“I was mortified,” Colbert admitted years later during an interview.

“I was trying to impress her, and instead, I basically embarrassed myself in front of her entire family.

It was like bombing my own love audition.”

Despite his nerves, Colbert didn’t get Evelyn’s number that night.

He went home kicking himself, convinced he had blown it.

But destiny — and a pair of very kind parents — had other plans.

Days later, while he was out in town, Evelyn’s parents ran into him again.

Remembering his clumsy attempt, they decided to play matchmaker.

“They came up to me and said, ‘You know, our daughter thought you were very nice,’” Colbert once shared, smiling.

“And I couldn’t believe it — after all that awkwardness, they were actually helping me.”

It turned out that Evelyn, too, had been struck by that brief encounter.

Through a few friendly nudges from her parents, the two reconnected, this time without the pressure of an audience.

From there, a genuine connection grew — built not on charm or confidence, but on shared humor, sincerity, and what Colbert jokingly calls “mutual weirdness.”

The two began dating, and soon it became clear that this was more than just another chapter in Colbert’s life.

Evelyn, a fellow South Carolinian and actress, understood his quirks, his insecurities, and his creative drive.

When Colbert’s career took off — from his early days on The Daily Show to his legendary run on The Colbert Report and later The Late Show — she remained his anchor.

Colbert has often credited Evelyn for keeping him grounded through the chaos of fame.

“She’s the reason I’m able to do what I do,” he once said.

“She’s not impressed by any of this.

She’s impressed if I remember to take out the trash.”

Fans adore the story because it reveals a softer, more human side of the comedian known for his biting wit.

In a world of celebrity relationships built on image, Colbert and Evelyn’s love story stands out precisely because it started with awkward honesty and a little bit of parental intervention.

Today, more than 30 years later, the couple is still together, raising three children and sharing a quiet life away from the spotlight.

Colbert has joked that he still owes Evelyn’s parents “the biggest thank you in the world” for saving him from his own nervousness that night.

Looking back, Colbert laughs at how something so humiliating could turn into something so meaningful.

“I was just trying to ask a girl for her number,” he said with a grin.

“And I ended up finding my whole life.”

It’s a story that proves sometimes, even the most awkward beginnings can lead to the most beautiful endings — if you have the courage to show up, stumble through your words, and let fate — or a pair of meddling parents — take care of the rest.