The Wooster Street Social Club (aka NY Ink) is finally a success and now new problem are in the future including the balance of work and family.
With the shop doing so well, Ami throws a party to celebrate and it turns bad when Megan invites Chris without asking Ami first. Jessica tries again to move closer to becoming a tattoo artist someday.
Ami has been allowing Billy to do small tattoo for a short time and now it is his chance to work on a more elaborate one. Tila Tequila wants a tattoo to memorialize her parents andsuggestive pictures of Megan are creating a big stir.
Ami is missing his little girl and he takes Tommy to South Beach. They stop in and hang out with the crew from Love/Hate (aka Miami Ink).
Ami is inspired to give back to troubled teens by inviting them to the shop. However when the crew's joking upsets Robear, his fury almost ruins the good will.
The tensions between Ami and Billy break and Billy must now decide between friendship and his apprenticeship. The girls set Robear up on a speed dating event.
Now that Billy has quit Wooster Street Social Club, he needs to make it as a tattoo artist and asks for Chris's help. Megan is falling in love with a friend and worries it will ruin the friendship if it doesn't work out.
Megan gets a NY apartment, Tim misses California and wants to go surfing and drags Ami with him. Tommy sees the tattoos Jessica has been doing on the side and ruffles feathers at the shop.
Ami must decide whether to fire or train Jessica to tattoo, when it comes out that she has been tatttooing out of her house. Megan moves into the apartment she found, however Joey (her new boyfriend) has his own thoughts for them.
Ami confronts Chris regarding the trash talk of Wooster Street, while Megan decides whether to follow love or career. Ami is looking for a partner to help run the shop and asks Tim to fill the role.