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Joy is in her late thirties and is ready to settle down, but when her relationship goes up in flames, she decides to let loose and have some fun, constantly being placed in hilarious situations with her friend Liz as they navigate the worlds of dating, drinking, and heartache.
Joy Montgomery is a thirty-seven-year-old professional who is always the bridesmaid and never the bride. She is more than ready to settle down and get married, and when she meets Ryan at her friend’s wedding, she thinks her time has finally come. Things go awry however, and her relationship falls apart when what she thought was a marriage proposal turns into a massive misunderstanding. Liz, a twenty-five-year-old employee at Joy’s company, tells Joy to go win back Ryan by surprising him late at night. Joy takes this advice and ends up walking in on Ryan and her coworker and former sorority sister, Carmen having just had sex.
Completely heartbroken, Joy decides to take Liz up on her offer for drinks and learns to let loose, have fun, and not take everything so seriously. Liz walks Joy through her various rules for things such as curing a hangover, turning a walk of shame into a walk of fame, and of course: the rules of day drinking. Joy continuously finds herself in hilarious, ridiculous situations brought on by partying and alcohol, but learns to be independent once more and not rely on someone else to make her happy.
When Joy is forced to see Carmen and Ryan again at her friend’s house warming, she learns that not only did Ryan sleep with Carmen after their breakup, but had been seeing her during the early stages of their relationship too. Angry and hurt, Joy goes to the bar looking for Liz and meets Alex. He is kind and understanding and Joy starts to believe in love again. When Liz tells her to be careful and that all guys are the same, Joy gets angry and they get in a huge fight. Just when Joy thinks things can’t get worse, Carmen comes in and starts a confrontation. This is the final straw for Joy, and the two get in a huge fist fight in the middle of the office that results in them both getting fired and ending up in a hospital.
Ryan visits Joy and the two say a final goodbye, letting each other go and deciding to move on. Liz and Joy make up as well and Joy helps Liz prepare for a date. The story ends at the bar with Liz and her new boyfriend, and Joy and Alex, all happily drinking together, ready to embark on the next chapter of their journeys.