Rob is a recently single radio show producer broker who moonlights as an anonymous dating advice guru known only as 'Ask Joe'; unbeknownst to his loyal followers, he struggles to hold on to a girlfriend himself. Clint, Rob's best friend, is a former supermodel whose fear of getting older (he just turned thirty!) results in an existential crisis, leading him to trade in the gym for booze and paid escorts. Scott, former band member/roommate of Rob's brother, Avery, finds himself brokenhearted and living on Clint's couch when his fiancée decides not to follow him to New York. Freddy, the youngest of the crew, works to find balance between his life as an aspiring actor and being a good single father, all the while trying to decide between rekindling things with his ex or leave the past behind him starting something new. Together these four friends band together in their pursuit of meaningful relationships while battling the confusion of what it means to be an adult in your thirties.