Fifth Avenue in the Gaslamp Quarter was a red-light district called the Stingaree, named after the stingrays in San Diego Bay, where Wyatt Earp ran gambling halls and 138 prostitutes were arrested in a single raid. It is now one of the most social streets in California. Whiskey Girl has been at the heart of it since 2004.
Before it was the Gaslamp Quarter, it was Rabbitville.
That is not a joke. In the 1850s and 1860s, before Alonzo Horton arrived and decided to build a proper city on San Diego Bay, the area that would become downtown was so desolate and so repeatedly unpromising that early settlers, in a moment of resigned wit, named it after the only creatures who seemed to find it habitable.
The rabbits, presumably, did not appreciate the honour.
Then Horton arrived, bought up the waterfront, built a wharf at the end of 5th Avenue, and started selling land. Within a few years the area was booming. The city installed around fifty gas lamp street lights — the new modern part of town deserved illumination — and the name New Town gradually became the Gaslamp Quarter.
And then the gamblers arrived.
🎲 The Stingaree: Wyatt Earp, 138 Prostitutes, and a Street Named After a Stingray
By the 1880s, Fifth Avenue had a problem.
Or, depending on your perspective, it had an extremely lively solution.
As commerce moved northward, the lower end of downtown — the blocks around 5th Avenue closest to the waterfront — became home to what a San Diego Union reporter, walking the street in 1887, described in terms that leave nothing to the imagination: "asthmatic pianos, discordant fiddles, and drunken voices boisterously singing ribald songs… men lying drunk on every corner… fully as bad as the Barbary Coast in San Francisco."
The neighbourhood became known as the Stingaree — named for the fierce stingrays in San Diego Bay, which locals considered an apt metaphor for a district that would sting you if you weren't paying attention.
Wyatt Earp — lawman, gambler, legend — ran three gambling halls here. The Victorian buildings that line the Quarter today were built on top of this history, their upper floors occupied by establishments that made the neighbourhood infamous and the lower floors by the saloons and bars that served everyone who came to participate.
In 1912, the city announced it would host the Panama-California Exposition and needed to present a more respectable face to the world. Police raided the Stingaree and arrested 138 prostitutes in a single night. 136 promised to leave the city. Two agreed to reform. The next morning, one changed her mind. The other was found to be insane.
The Stingaree declined. The navy used the district. The postwar era brought peep shows and adult bookstores through the 1970s. And then, in one of the great urban reversals, property owners and city leaders decided the Victorian buildings were worth saving, created a preservation plan, and slowly transformed the most notorious street in San Diego into one of its most beloved.
The gas lamp street lights stayed. The Victorian architecture stayed. The name stayed. The energy of a street that has always known how to have a good time — that part stayed too.
🥃 Whiskey Girl: On 5th Avenue Since 2004
702 Fifth Avenue. Corner of 5th and G Street.
Whiskey Girl opened in 2004 and has been going ever since — one of the longest-running entertainment venues in the Historic Gaslamp Quarter, which in a district with this much turnover is a genuine distinction.
The venue has over 70 whiskeys. San Diego craft beer alongside domestic favourites. American classics on the food menu. Live acoustic music nightly, followed by DJs. Sports packages for every game worth watching. A Sunday brunch. A patio. The kind of social energy that the Gaslamp has always generated — refined now, legal now, considerably more cheerful than the Stingaree — but with the same underlying quality that has made this block magnetic for 140 years: people come here to be around other people.
Nightclub & Bar listed it in their Top 100. The venue supported the Boys & Girls Club of Barrio Logan for three consecutive years of toy drives. It has been the official after-party location for the Rock 'n' Roll San Diego Marathon. It is, in the most genuine sense, a community fixture as well as a destination.
Which is exactly what the street has always produced.
☀️ San Diego Dating in 2026
San Diego has a dating reputation that is simultaneously glowing and slightly frustrating.
The glowing part: the city is genuinely beautiful, the weather is perfect roughly 300 days a year, the outdoor culture produces people who are active and present and comfortable in their bodies, and the general vibe is warmer and more laid-back than either LA or San Francisco.
The frustrating part: that same laid-back quality can translate, in the dating context, into a certain diffuseness. People are happy here. They have their outdoor hobbies, their beach communities, their established social circles. The urgency to expand those circles — the friction that creates social encounters in harder cities — is somewhat absent when the sun is shining and the Pacific is a mile away.
The apps in San Diego have a particular quality. They feel almost too comfortable. Everyone is attractive. The photos are excellent. The profiles mention hiking and craft beer with a specificity that suggests both are genuine interests rather than strategic posturing. And then the plans somehow never quite get made, because there is always a better beach day to wait for.
A MyCheekyDate evening at Whiskey Girl cuts through all of that.
You are on Fifth Avenue — a street that has been reliably producing social encounters since Alonzo Horton built the wharf. You are at one of the Quarter's longest-running venues. You have a specific reason to be there, a structured format that removes the ambiguity of whether the person across from you wants to talk, and four minutes to find out if there is anything real.
The weather outside is perfect. There is no better beach day to wait for. This is the evening.
😏 Why the Gaslamp Works
There is a quality to the Gaslamp Quarter that is different from most entertainment districts in most American cities.
It is genuinely walkable. The Victorian buildings give it a human scale that corporate redevelopment zones don't have. The streets are full of people rather than cars. And the history — the fact that this block has been doing this, in one form or another, since the 1870s — gives it a weight and a character that newer neighbourhoods simply cannot manufacture.
Walking down Fifth Avenue on a Saturday evening, you feel that you are part of something that has been going on for a long time and will continue for a long time after you leave. That feeling — of being somewhere that has accumulated genuine history rather than simulated it — is good for dating in the same way it is good for any human activity.
It makes you feel like you showed up for something real.
📍 The Events
Ages 24–36 | Saturday Nights | Whiskey Girl, 702 Fifth Ave, Gaslamp | 7PM Early Bird from $32.95 → Book here
Ages 27–42 | Sundays | Whiskey Girl, 702 Fifth Ave, Gaslamp | 7PM Early Bird from $32.95 → Book here
Ages 32–44 | Select Dates | Whiskey Girl, 702 Fifth Ave, Gaslamp | 7PM Early Bird from $32.95 → Book here
Full schedule at mycheekydate.com/speed-dating-san-diego
🥂 The Cheeky Truth About San Diego Dating
San Diego does not need better apps.
It needs more evenings where the format matches the city's natural energy. Where showing up somewhere great, with a specific purpose, with good people around you, produces the kind of easy, warm, present conversation that San Diego people are actually excellent at — when the context is right.
The Gaslamp Quarter is that context.
The street that went from Rabbitville to red-light district to Victorian revival to one of the best social miles in California.
Whiskey Girl has been part of that story for over twenty years.
And the person across the table might be exactly who you were looking for.
Order the whiskey. The stingrays in the bay are centuries removed.
The rest is just conversation.
MyCheekyDate has hosted over 1,100 speed dating events in San Diego. Host-led. Smart-Card matched. No Stingaree, no gambling halls, no Wyatt Earp. Just Fifth Avenue, over 70 whiskeys, and four minutes to find out. Find your San Diego event →