Teddy B’s Bar

I was only here once, killing time before a flight, practicing my jump-​shot. Hogged the pool table until who I assumed to be a regular slapped her quarters down… she looked meaner than me, so I gave it up.
Service attentive, atmosphere friendly to newcomers.
Little slots in the wall so your cue doesn’t roll onto the floor!

This is the joint that all those guys from a police line up mug shot go after they get their picture taken by the police photographers. Teddy B’s is unapologetically a dive bar. Inhabited if not infested by hoary locals and a supporting cast of bizzare strays, Teddy B’s was built for a David Mammet flick. There’s low level hustling at the pool table and a crusty looking geezer will try to hustle you out of ten bucks in a rigged game of craps. The prized attraction of the joint is the Amy the bartender, a woman with more pep than the energizer bunny, a sharp mind that remembers your name and your favorite drink from a single mention, and the good sense to keep you from drinking yourself into a stupor. Tuesday nights, a local R&B covers band takes stage by the jukebox. These guys are old school and know how to rock the house without the latter-​day rock and roll theatrics. Come here for a decent drink and a bit of local color but don’t expect a thriving singles scene. The hipster element in San Mateo has yet to get Teddy B’s on their radar.

After drinking the strongest Long Island Iced Tea OF MY LIFE at this bar, I proceeded to wash my hair in the sink of Heidi’s Pies (located across the street). I don’t know if this is the sign of a good time or a time gone horribly wrong. You can’t bring your drinks on the back patio here and I found this to be a mixed scene. Good place to spot some San Mateo natives.

Teddy B is a friendly Irish dude who wears sunglasses indoors and looks like he should either be a radio DJ, or should live in a chair next to a pool with a stiff drink in his hand. The bar pulls in an older local crowd (some of who show up at opening at 6AM), who in my one visit here during the week were really friendly and overly chatty, and on my one weekend visit seemed to have a number of iron-​liver-​club members and potential brawlers. There’s been live music both times I visited and a row of Harleys in the back last night.

The bartender here made me the strongest Long Island of my life, and for that they have gained my respect. Come here if you want to mingle with quirky locals and get a true ‘dingy Peninsula bar’ experience (I’m sure everyone does…)