Halfway into his final show on Friday, before leaving to take over as moderator of "Meet the Press," Todd informed viewers that his producers had arranged a surprise guest to send him off, which at first appeared to be White House press secretary Josh Earnest.
But after a brief exchange, Earnest revealed the true surprise was Todd's former "Rundown" co-host Savannah Guthrie, who departed in 2011 to join "Today".
Guthrie, currently on maternity leave for "Today," was standing by via Skype.
The delay on Skype created problems.
"Well, Miss Mama Guthrie," Todd began. "Can I call you Mama Guthrie?"
About ten seconds of silence ensued.
"Hi, Chuck," she responded.
"Hi, Savannah," he replied.
From there, it got awkward.
The two spoke over each other for several seconds until one of many long silences of the segment took hold. Finally, Guthrie asked, "Do you see all the pictures that we got going?" Todd appeared confused until an image appeared onscreen of him holding Guthrie's infant daughter.
"She was one beautiful girl," Todd remarked. "That was one of my favorite days of the year. Was being able to hold your lovely daughter."
Guthrie did not respond for roughly fifteen seconds, simply staring at the screen, both of them in complete silence.
"Aw," she finally replied.
For the full awkward experience, watch the clip below: