The actress was introducing the 30th anniversary tribute for The Breakfast Club when she said to the audience: "I was part of a club that made history, but now can I be in Taylor's club please?"
A few moments later, during Simple Mind's performance of "Don't You (Forget About Me)" from the film, Ringwald was seen in the front row enjoying the performance with none other than the "Shake It Off" crooner herself.
After the two sang and danced along to the 1985 classic, and the broadcast was about to go on a commercial break, Swift appeared to be giving her new best friend her phone number.
Who knows if this friendship would have sparked sooner, the Sixteen Candles star could also have been in the singer's star-studded "Bad Blood" video.
The singer, who offered a slew of GIF-worthy moments during the show, did not leave the MGM Grand's Garden Arena in Las Vegas empty handed. She won eight awards including Top Female Artist and the Top Billboard 200 award.