1 The Haven Jamaica Plain 284 Amory St Boston Monday trivia and scotch eggs A proper pour of single malt My most loyal infidelity. I always come back on Mondays! 2 Brendan Behan Pub Jamaica Plain 378 Centre St Boston No TVs, just conversation Guinness, obviously Cash only, phone-free feeling even if you brought yours. Pure JP. 3 Eugene O'Neill's Pub Jamaica Plain 3700 Washington St Boston Tuesday trivia, Sunday brunch Whatever's on the cocktail special board My Tuesday team has strong opinions and weak general knowledge. We persist anyway. 4 Jeanie Johnston Pub & Grill Jamaica Plain 144 South St Boston Wednesday trivia, karaoke chaos A cold domestic draft, no frills Dive bar energy in the best way. Someone is always mid-karaoke-crisis and I love it. 5 Costello's Tavern Jamaica Plain 723 Centre St Boston Low-key weeknight pint House lager Unfussy and a little worn-in, like a good coat. No notes. 6 Samuel Adams Boston Brewery Jamaica Plain 30 Germania St Boston Trivia with a brewery backdrop Boston Lager, fresh off the source Feels a bit like cheating to call it a bar, but the trivia counts and the beer is literally made feet away. 7 Tres Gatos Jamaica Plain 470 Centre St Boston A glass of wine and record browsing Spanish red by the glass Where I pretend to be a sophisticated adult for one evening before buying a used record I don't need. 8 Doyle's Cafe Jamaica Plain 3484 Washington St Boston History on every wall A well-poured pint of Guinness The old photos alone are worth the visit. Bring a friend who likes trivia and local lore in equal measure. 9 Midway Cafe Jamaica Plain 3496 Washington St Boston Live music and queer dance nights Whatever's cheapest on tap Tiny, loud, a little chaotic. Perfect for when trivia feels too quiet. 10 Galway House Jamaica Plain 720 Centre St Boston Striking up a conversation at the bar A classic Irish pour Sit at the bar, not a booth. That's the whole trick.