Grape & Grain
227 South San Mateo Drive
San Mateo, CA 94401
If you’re a wino or beer lover looking to meet like-minded drinkers, the Grape & Grain is the perfect place to start. Located in downtown San Mateo, this wine and beer bar provides the perfect relaxed setting in which to either get to know someone you’ve just met or meet new people in a no-pressure environment. Patrons can be found lounging around on couches, doodling on the chalk board wall, or chatting about a new and unique beer they just tasted. The extensive wine and beer menu at Grape & Grain is enough to inspire conversation, and the small plates menu provides just enough food for two to complement your drinks. TVs and board games do not detract from the trendy decor, but instead add to the bar’s down-to-earth attitude.
215 East 4th Avenue
San Mateo, CA 94401
This laid back, casual bar draws a crowd with free pool, darts and peanuts, but keeps the regulars coming back with friendly bartenders, live entertainment and plenty of TVs for catching the game. There is plenty of space to relax and mingle, with booths lined up on one side of the bar and tables down the center. A jukebox provides the bar’s musical entertainment, but there are usually live bands playing on the weekends. If you really want to open up, stop in to McGovern’s on Thursdays for karaoke–you’re sure to meet some outgoing individuals who aren’t too shy to strike up a conversation.
Related: 12 Best Bay Area Sports Bars
The Wine Room
520 Ramona Street
Palo Alto, CA 94301
A charming wine bar located in downtown Palo Alto, The Wine Room transports you to a homey, country cottage as soon as you step through its doors. Complete with a fireplace and tapestry pillows, the living-room style area in the back part of the bar is an inviting place to kick back and relax. The bar’s “lite fare to share” menu provides the perfect opening line if you’re mulling over a way to introduce yourself to the cute guy or girl sitting alone at the end of the bar. This popular wine bar can get quite packed on the weekends, but it still retains its friendly and welcoming atmosphere–all the more reason to say hello to someone new.
Related: San Francisco’s Coziest Bars
The Downtown Tiki Lounge
144 South B St.
San Mateo, CA 94401
Nothing lightens the mood or lessens the tension quite like being on vacation, and at the Downtown Tiki Lounge in San Mateo, you get all the great vibes of a Caribbean getaway without the steep airfare prices. Stop in for happy hours (weekday from 4 to 7 p.m.) for cheap drinks and appetizers, or come in later and sip on deliciously fruity specialty cocktails, like the Blue Hawaiian or Tiki Tea, that will transport you to a tropical paradise. The menu offers some delicious bites without going overboard (try the grilled cheese or pot stickers), and the lounge has a great mix of tabletops, couches and bar stools, so you can choose a setting in which to mingle and meet others. If you come with a few of your best wingmen or your favorite group of single girlfriends, order the “Volcano Bowl.” It’s a delicious, 48 ounce concoction that will have the whole group singing “Two Tickets to Paradise” before the night’s end.
1166 Geneva Ave.
San Francisco, CA 94112
Best known for its appearance on Food network’s “Diner’s Drive-Ins and Dives,” the Broken Record fits into the show’s latter category. While this is a dive bar in the standard sense, it’s also one of the best places for delicious bar food in South San Francisco. A whiskey bar at heart, the Southern-style dishes at the Broken Record are unrivaled in the dive bar scene. The atmosphere is unpretentious and the setting provides the perfect mix of music and regulars that allows patrons to kick back, select their poison of choice from the large whiskey menu, and converse with others over some great eats. Just remember that this is a cash only bar, or you’ll end up ruining the evening by making your new found friend pick up the entire tab.