Abraham Aguirre and Mikayda Mills two step on a dance floor at Two Step Inn at San Gabriel Park in Georgetown, Texas on Sunday, April 6, 2025.
Aaron E. Martinez/American-Statesman
Valentine’s Day has a way of making even the most self-assured people take inventory. Not of their reservations or gift ideas, but of their dating history — specifically, the moments that went wrong in ways too specific to forget. I’ve lived in Austin mostly single, which means I’ve accumulated a personal archive of misfires.
Austin is a city built for romance, but it’s also a remarkably efficient place to learn what doesn’t work. I’m not alone. As of 2025, roughly 44 percent of Austin’s population is single. Dating here is less about finding perfection than navigating a series of near misses, each one clarifying what you can tolerate, what you can forgive and what you absolutely cannot.
Article continues below this ad
What follows are five first dates that didn’t lead anywhere, but did leave me with a sharper understanding of who I am and how I want to show up with other people. I share them as field notes — from Austin bars, dance floors and concert venues — offered in the hope that recognition might spare someone else the same awkward lesson.
Why Barton Springs isn’t a confessional
People swim during the annual Polar Bear Plunge at Barton Springs Pool in Austin, Thursday, Jan. 1, 2026. The spring-fed water at Barton Springs maintains a temperature of about 68 degrees.
Mikala Compton/Austin American-Statesman
Vulnerability is good on a first date. Honesty is good. Emotional availability is supposedly the whole point. But asking a near-stranger to be your primary support system on a sunny afternoon at Barton Springs Pool — as one potential beau did — is a decidedly ambitious move.
Article continues below this ad
Barton Springs is not a confessional. It is a place for cold water, loose conversation and the mild fantasy that everything in your life is briefly fine. It is not where you unpack unresolved breakups, recent family conflicts or a list of career regrets.
I am not opposed to vulnerability. I just don’t excel at managing other people’s emotional revelations while submerged in 68-degree water. There is something disorienting about treading water as your date catalogues their personal disappointments, each one hitting like a splash from the diving board.
Kit Baumann, right, and Aliza Orent react to the cold during the annual Polar Bear Plunge at Barton Springs Pool in Austin, Thursday, Jan. 1, 2026. The spring-fed water at Barton Springs maintains a temperature of about 68 degrees.
Mikala Compton/Austin American-Statesman
What, exactly, is one supposed to do in that moment? There is no correct response. You listen. You float. You silently wish for a reset.
Article continues below this ad
The lesson, if there is one, is simple. On a first date — especially at a joyful public place that’s as emotionally neutral as Barton Springs — it’s best to travel light. Bring curiosity. Bring sunscreen. Leave the baggage at home.
Austin concerts are sacred, so choose your date wisely
Fans pack into the Germania Insurance Amphitheater to see F1 drivers speak during fan experiences at the Formula 1 Pirelli United States Grand Prix at Circuit of the Americas on Saturday, Oct. 19, 2024.
Aaron E. Martinez/American-Statesman
The Germania Insurance Amphitheater at Circuit of the Americas holds some of my most memorable Austin memories: seeing Lana Del Rey under the Texas sky, dancing to Kygo after Formula 1, and — less triumphantly — being trapped in a car with a man who felt compelled to demonstrate his authority on reality television.
Article continues below this ad
It was the summer of “Love Island,” a season Austin took personally. Allegiances were declared at watch parties, debated at bars and occasionally broadcast on dating profiles. So when my date brought it up after Willie’s Fourth of July Picnic, I assumed it would be lighthearted — a way to pass the slow crawl of traffic back into town. This assumption was wrong.
Willie Nelson performs at his Fourth of July Picnic in Austin at the Germania Insurance Amphitheater on July 4, 2025.
Ana Gutierrez / Austin American-Statesman
My date had never seen the show. Not one episode. Still, in the spirit of modern confidence, he had plenty of opinions. I tried to meet him halfway. When I pointed out that he hadn’t actually watched it, he went quiet.
There are few things more uncomfortable than a silent car ride with a first date, especially when it arrives after a conversational collapse and unfolds at five miles per hour. What should have remained one of the best concert nights I’ve had in Austin became permanently attached to that stalled drive and its half-baked argument.
Article continues below this ad
If there is a lesson here, it’s this: protect your experiences. Choose your concert companions carefully — especially when the venue is an hour away and the ride home leaves no room to escape.
Keep your Juul in your pocket at AFS
AFS Cinema is run by the Austin Film Society, which was founded by Richard Linklater in 1985.
Austin American-Statesman
If you’ve never been, the Austin Film Society Cinema is an arthouse shrine: industrial lightbulbs glowing, movie posters lining the walls, a bar humming with people who seem to possess a private language built out of directors’ cuts. It’s the kind of place that makes you want to earn your seat.
Article continues below this ad
It’s also the kind of place where forgetting yourself is easy — unless your first date has no working knowledge of cinema etiquette. The rules, to me, were obvious: no talking, no phones, no aggressive snacking. What never occurred to me was the need to explicitly ban vaping until my date casually produced a crackling Juul mid-screening.
Time and place matter. There was a moment in cinematic history when people smoked in theaters, when Hitchcock’s “Rear Window” premiered under a haze of cigarettes and social permission. This is not that moment. In this era, people insist they don’t vape while actively vaping, a contradiction best left outside.
A poster for Alfred Hitchcock’s 1954 mystery film ‘Rear Window’ starring James Stewart.
Movie Poster Image Art/Getty Images
There was also the context: we were watching “Wild at Heart,” only days after David Lynch’s death, in what is arguably the most sacred movie house in Austin. This felt less like a personal quirk and more like a misunderstanding of the room.
Article continues below this ad
We remained friends. No harm done. But the lesson is straightforward. On a first date — and especially in a place built on collective reverence — courtesy is not optional. And for the love of cinema, keep your Juul in your pocket.
Leave room for possibility — and skip the last shot
A Smokey Frozen Margarita is served at Old Pal Texas Tavern on Friday, June 20, 2025 in Lockhart, Texas.
Aaron E. Martinez/Austin American-Statesman
Consider this a warning to anyone who loves tequila and believes in first impressions. A first date already demands optimism and the ability to appear charming while pretending not to care. Alcohol does not improve these odds. Tequila, in particular, tends to make them worse.
Article continues below this ad
The mistake begins innocently enough. You meet friends for a quick drink at a place like De Nada or Polvo’s, where margaritas arrive with the confidence of someone who has never suffered consequences.
There is always a final shot — the one taken out of misplaced faith that courage can be distilled. This is incorrect. I learned this at Mohawk, the kind of venue where effortlessness is the dress code. Daydream Twins played. My date and I talked and drifted toward Big Topics, testing alignment.
Gurriers performs at Mohawk in downtown Austin at SXSW Friday, March 14, 2025.
Ricardo B. Brazziell/American-Statesman
Artificial intelligence entered the conversation, a loaded subject in Austin where tradition is trampled by innovation, whether it’s self-driving cars or app-run everything. We did not reach a compromise. Instead, my body reached a conclusion. I excused myself and made a swift calculation involving the nearest trash can.
Article continues below this ad
My date was gracious, but we never saw each other again. The lesson has little to do with tequila and everything to do with restraint. It’s about leaving enough room for possibility. And tequila has a way of filling the space where that possibility might otherwise live.
When you can’t lead at the White Horse
Viva Big Bend Launch Party Thursday, June 28, at The White Horse Saloon
Austin 360
A first date at a two-stepping bar is a small act of faith. At the White Horse, that faith is amplified by sweat, live fiddle and the unspoken understanding that someone is expected to lead.
Article continues below this ad
The White Horse on a good night is pure Austin choreography: Lone Stars sweating in hands, couples moving in confident, circular patterns as if they were born knowing when to turn. My date did not know his left foot from his right. This, on its own, is not a crime. Everyone starts somewhere. But in a space where the lead is traditionally offered — and taken — hesitation reads loudly.
Eventually, someone else asked me to dance. This is normal at the White Horse. It’s a place built on shared movement. I said yes. For a moment, I almost reached joy — caught in the rhythm, carried by someone who knew exactly where the music was going.
Attendees dance at Two Step Inn at San Gabriel Park in Georgetown, Texas on Sunday, April 6, 2025.
Aaron E. Martinez/American-Statesman
Then I opened my eyes and saw my date watching from the edge of the floor, expression tight with something that looked like disapproval. Whatever it was, it hovered between us when I returned, heavier than the music. We never quite found our footing again.
Article continues below this ad
On a first date — and especially at a place like White Horse — understand where you stand. If you can’t lead, be willing to follow. If you can’t dance, don’t begrudge the dancers.