Sharyn, from Edge Afternoons, revealed that she missed out on an important high school moment that many of us have experienced.
After leaving school at 15, Sharyn never got the opportunity to go to her school ball.
Upon hearing this information, Steph suggested that Sharyn should have the chance to re-enact that special moment of asking someone to the ball.
Then the question came of who would have been the person Sharyn would have asked at the time if she had had the chance.
You might remember last year, we discovered Sharyn's teenage songbook, which she used to write angsty songs about teenage life, love, and heartbreak.
You might be wondering who inspired some of those heartbroken tunes.
Sharyn revealed it was her crush, Anthony.
So who better to hypothetically ask for a ball than him?
Steph, Nickson, and a reluctant Sharyn decided to call him together to ask the big question.
You could say Sharyn was freaking out a bit.
They gave him the call and Sharyn could not contain her awkwardness about the situation.
Just before asking the question, Steph popped in to ask whether Anthony was Sharyn's first kiss.
"No, we've never kissed" Sharyn responded.
Across the phone, you can hear Anthony respond with an 'ew' which sent the team into hysterics.
Finally, time to get down to the nitty-gritty..
After Sharyn tried her best to stall and prolong the uncomfortable question, Nickson had to step in.
"If Sharyn asked you Anthony 'Would you go to the ball with me?' at that time, would you have said yes" he explained.
It didn't go as smoothly as we thought.
After some awkward silence, which Anthony tried to pass off as issues with the signal, he finally revealed his answer.
"I wouldn't have gone."
I guess you could say it's not the way we anticipated her big moment would go.
Watch the awkwardness unfold in the video above or listen to the podcast episode below.