No one likes missing the beginning of post-work drinks to wedge in a haircut -- by the time you show up, your friends are too sloshed to compliment you on your haircut. To ensure their inattention doesn't wound you, get drunk yourself, at Old Glory Barbershop.
Old Glory's a hallowed, nautically-themed Main Street shop helmed by a trio of barbers as dedicated to making your hair look good as they are to making sure you're buzzed enough to be cool if it doesn't. Each reasonably-priced cut comes with a free Red Stripe, whether it's the $15 "buzz", the $25 "short", or the $40 "long" -- designations that seem excessively simple to most, but painfully confusing to Boy George. Mention Thrillist, and OG'll also pour you a shot of Patron, a shot of Jameson, or, if you're not afraid to look a gift horse in the underside of the chin, a shot of both.
As luck would have it, OG's also got an in-store tattoo parlor, which you might just get bombed enough to take advantage of -- if your friends don't notice the Hula Girl on your neck, they're not really your friends.