Gomez's last Late Show appearance came last year while she was still dating the teen heartthrob, so Letterman got an update on how Gomez has been coping.
After Gomez confirmed that she's not currently seeing anyone, Letterman joked that he made Bieber cry the last time the singer visited the show.
"Well then that makes two of us," Gomez quipped, earning a hearty applause break from the live audience.
How will the biebs feel when he hears this Gomez is currently promoting her upcoming film, Spring Breakers, out March 22
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