Devastated by his break-up with Brett, Kenny tags along with Pat and Jimmy to a Lonely Hearts happy hour, but when they try to use Kenny’s sadness to get attention from single ladies, Kenny inadvertently steals the show. Meanwhile, Eileen shuns the usual Valentine’s Day traditions until a chance encounter changes her mind.
Jimmy wants to teach his younger brother the rite of passage of drinking. When Shannon gets a comp hotel room due to a scam she’s pulling, Jimmy thinks this is the perfect time to teach Kenny how to drink, but it all goes awry when Kenny invites Brett to join in. Meanwhile, Eileen discovers that Pat has a new girlfriend, her nemesis, Sheila DeMars.
Kenny’s jealousy over Brett’s relationship with his best girl friend leads Kenny to realize he’s been a bad friend to Allison. Jimmy and Shannon start their own ridesharing company. Meanwhile, Eileen and Pat are shocked to catch Clive “cheating” on them.
After Kenny and Brett officially become a couple, Kenny starts to think of plan on how he should break the news to his parents. Meanwhile, Jimmy surprises everyone when he scores a high SAT score, forcing Eileen to hold up her end of a deal that she had previously made and takes Jimmy car shopping.
The O’Neals deal with a change to their Thanksgiving tradition when Pat and Eileen invite Gloria and VP Murray to dinner as their dates. Meanwhile, things don’t go as smoothly planned when Gloria offers to help Kenny cook, and Eileen prepares to meet VP Murray’s mom for the first time.
A contemporary take on a seemingly perfect Catholic family, whose lives take an unexpected turn when surprising truths are revealed. Instead of ruining their family, the honesty triggers a new, messier chapter where everyone stops pretending to be perfect and actually starts being real.