He risked it all to try and win the heart of Bachelor contestant Cassie Randolph.
And it looked like his bet paid off, as Colton Underwood and the object of his affection enjoyed their first 'official' date as a real couple this Thursday evening.
The new couple looked smitten while attending a sold-out performance of Frozen's Broadway adaptation.
Date night! Colton Underwood and girlfriend Cassie Randolph had their 'first' real date since leaving the show when the attended a performance of Frozen Live on Thursday
After the show the duo were even invited on stage by star Patti Murin, who plays Ann, for the curtain call.
Introducing the pair, the actress said: 'There are two people here who are on their first date.'
The crowd responded with cheers, already aware of the reality royalty in their midst.
As they stepped onto the stage, the couple looked like the perfect pair.
Cassie donned a leggy grey suit-inspired frock while Colton looked dapper in his usual uniform of a jacket, jeans and tee-shirt.
Packing on the PDA: Cassie and Colton kissed on stage while the crowd dispersed
Stage presence: After the show the duo were even invited on stage by star Patti Murin, who plays Ann, for the curtain call
Though Underwood was used to giving out the roses, this time Randolph received a beautiful bouquet from a pint-sized part of the cast.
The pair were greeted with big hugs, before the former NFL player shared a few words.
'I didn't realize the parallels between Frozen and The Bachelor,' he said.
Patti jumped up and down with glee, telling Colton: 'I was thinking about you guys the whole