We’ve all sent super embarrassing text messages to someone we like…it’s a rite of passage in the digital era!

Maybe you made a painfully awkward typo or you sent the wrong emoji. And waiting to hear back from your crush seems like an eternity sometimes!

Tonight Show host Jimmy Fallon and his guest, Sting, recently took turns singing some of these ridiculous first text exchanges.

One of the selected excerpts included poor Tim, who somehow sent the same text four times in a row!

Watch the entire clip below:


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