Unhinged, A Dating Series: Sipping Solo in Bars
Earlier last month, New York real estate maven Laurie Cooper made a call to singles everywhere: “Go sit at the bar this September to meet someone.” Posting on TikTok, the octogenarian influencer urged people people to “get off the apps” and into real life, recommending a roster of New York classics—The Carlyle, The Chelsea Hotel, The Gilded Age—that could serve as the perfect backdrop for a meet-cute.
It’s no secret that today’s daters are firmly fatigued with online apps and looking for screenless alternatives to meet up with other singles. How fitting, then, that an 86-year-old real estate broker should play shepherd to greener pastures. Everywhere, from The New York Times to Bon Appetit and The Washington Post, has declared “Sit at the Bar September” a movement, this year’s newest (oldest) dating trend. So why not keep it going in October in San Diego—one of the best, most crush-worthy months in the city?
While it might at first feel uncomfortably vulnerable to leave emotional-support friends, books, and screens behind, there’s nothing sexier than owning your solidarity and inviting friendly barkeeps and perhaps a lucky fellow single to join you in a drink. So, get into your main-character energy, be brave, and check out some of San Diego’s best watering holes to kick off your “Sit at the Bar October.”
The Classic: The Waterfront Bar & Grill
Tucked away somewhat unassumingly on Kettner Boulevard in Little Italy is one of San Diego’s oldest and still liveliest drinking establishments. Opened in 1933, The Waterfront Bar & Grill possesses San Diego’s longest-held full liquor license and is one of the city’s most packed bars (most times of the day). So, it’s a great place to try being on your own for the first time, because you’re always likely to meet at least one person. Plus, you’ll be in great hands with the incredibly friendly bartenders slinging stiff and affordable drinks. Grab a burger at the bar or get a basket of complimentary popcorn and see where the night takes you.
Who You’ll Meet
During the day, you’ll find the Little Italy local who’s been coming for years. They’ll introduce you to the bartender and tell you all the insider lore. At night, say hi to the young professional, ready to dump their high-stress job at the door and show you how to party Waterfront-style. Long Island iced tea, anyone?
The OG: Tivoli Bar and Grill
Tivoli opened in 1885 as a saloon and still features its original wooden bar inside. Known for being one of the city’s oldest watering holes, this Gaslamp Quarter dive bar is a favorite among locals, especially during baseball season. Head here before a Padres game and channel your inner Wyatt Earp. Order a whisky to give you some liquid courage and be ready to meet your soulmate—at the very least, you’ll come away with a history lesson and a story to tell.
Who You’ll Meet
The Padres die-hard who knows it’s much smarter to order $6 whiskey sodas for pregaming than it is to shell out for the $18 beer at Petco Park.
The Dive: Aero Club Bar
This much-beloved neighborhood spot off the 5 in Spruce Canyon supports a roster of regulars. It has all the trappings of a satisfying dive bar with strong drinks, friendly staff, flight-themed décor on every surface, and colorful Christmas lights strewn across the ceiling. (Because who doesn’t love a good holiday romance on a random Tuesday in October?) Aero Club is known for its whiskey collection, so consider having the bartender recommend one you’ve never tried and use it as a way to start a convo with the person next to you. Or, busy yourself with a round of pinball (the bar boasts a room dedicated to arcade games) while you work up your courage to approach the cutie playing Big Buck Hunter.
Who You’ll Meet
The tatted former hipster who’s buddies with all of the industry folks and can give you the rundown on their favorite ryes.
The Tiki: False Idol
Treat yourself to this speakeasy just south of Little Italy and rub elbows with true fans of tiki. Make sure to go on a weekday night when it’s less crowded but still lively enough to give you the opportunity to chat up a stranger. The bold décor and inventive drinks draw a diverse crowd, including bigtime tiki enthusiasts. And take it from us, the local scene in San Diego is full of interesting characters who you’ll want to spend your time speaking with. For drinks, rum is the name of the game. Grab a Painkiller and offer your barmate your best dad joke about its name—it’s sure to at least get a convo going.
Who You’ll Meet
They’re in full regalia for Tiki Oasis every year and might let you sample their homemade falernum if the night goes well. You can dance to Les Baxter in their palapa.
The Hot Spot: Happy Medium
This charming corner spot in North Park opened in 2024 and offers fresh takes on cocktail classics, delicious bar bites, and a youthful vibe. Though it’s popular, there’s usually a seat at the bar. Like any good neighborhood haunt, this place is often filled with locals talking about their latest vinyl purchase or which taco shop serves the best adobada tacos. Order a Super Grass (lemongrass mezcal, tequila, lime, mango, and pandan), then get cozy and people-watch from the bar. Pro tip: Talk music to the person sitting next to you; there’s usually someone nearby who will be excited to share their album recs.
Who You’ll Meet
They’re a bookseller at Verbatim Books by day and the DJ at Soda Bar by night. They’re sweet, passionate, and impossibly cool.
The Hotel: Nine-Ten Restaurant and Bar
The beauty of a hotel is that you’re sure to never run into the same crowd twice. Fresh faces and new opportunities are in high supply, and if you want the heady combination of new romance and a great drink, head to Nine-Ten, tucked inside the Grand Colonial Hotel in La Jolla. Striking the right balance of upscale yet laid-back, Nine-Ten draws an elegant and professional set looking for great food and a refined ambiance. You’ll find someone here to match your ambition and discerning standards. Start at the bar, and then head outside to the patio for a more private conversation.
Who You’ll Meet
The jet-setting sophisticate. They know their way around a wine list and might have a house in Monaco. You can impress them by ordering the pork belly.
The Brewery: Modern Times Beer
Looking to meet a surfy, down-to-earth cutie with great taste in hazy IPAs? Modern Times in Encinitas is the spot. Delicious brews and craveable vegan food draw in a host of outdoorsy, active North County types. The generous semi-circle bar means plenty of space to find a spot, and the chilled-out ’70s vibe makes chatting up your neighbor feel breezy. Plus, dogs are welcome, so bring your fluffy buddy for emotional support. It’s easily accessible right off the 101, so head over after your next wave sesh and see if someone catches your fancy.
Who You’ll Meet
The dawn patrol devout, who just got off work at Sun Bum next door. Their rescue dog is well-behaved, and they’re planning a trip to Hawaii next month. They’ll flirt with you over a Dungeon Map IPA and ask you for a walk on the beach afterwards.
If you’re new to Unhinged, catch up on all the dating chats you’ve missed here with columnists Nicolle Monico and Natalie Cooper. And follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each week.
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