It's not until after he's pulled the whole thing off that Jason realizes what a stupid move it was.

Tim and Jason go undercover as a just-married couple celebrating their honeymoon in order to catch a high-profile drug lord. Hand-holding, kissing, secret rendezvous and bed sharing ahead. OR: The JayTimWeek prompt I never posted, filled with all of my favorite tropes, inspired by Lana Del Rey’s song - Honeymoon

What started out as Jay jokingly sexting Tim in a bid to make him laugh (and, in his words, 'get that enormous stick out of his little ass') slowly turns into Tim not only no longer being angry with Jay, but, as they continue to jokingly sext each other whenever the instance arises, slowly starting to consider that a friendship may be blooming between them. After a while, it's possible that friendship could start to bloom into something even more, and maybe all that joke-sexting doesn't stay such a joke anymore after all.