ON FLIRTING WITH YOUR BARTENDER AND OTHER ACTS OF SELF-DESTRUCTION
- Tara R
- 1 day ago
- 3 min read
Updated: 18 hours ago

There is a moment — and every woman over 40 knows exactly the moment — when you realize you are flirting with your bartender and you have absolutely no business doing so.
It starts innocently. He refills your water without being asked. You make eye contact. You smile. He smiles back. And something in your brain — some ancient, pre-amortization, pre-school-pickup, pre-"have you seen my reading glasses" part of your brain — fires up and thinks: Oh. We're doing this.
We are not doing this.
And yet.
There you are, twirling your hair (you still have hair, thank God, though it now requires a level of structural engineering usually reserved for suspension bridges), leaning in slightly, laughing at something that was not actually funny. You are performing. You are performing flirtation the way someone performs CPR — desperately, with questionable technique, and with the nagging suspicion that it might already be too late.
The real question — the one that haunts you at 2 a.m. when you can't sleep — is: Is he flirting back, or is he just being nice because I'm a customer?
This is the central existential crisis of middle age. Not mortality. Not purpose. Not whether your 401(k) is going to be enough. It's reading the room when the room has exposed brick and a waitlist and the bartender's name is Jake and Jake is twenty-six and probably has a girlfriend named Kaylee who moisturizes with something that costs forty dollars and doesn't require a dermatologist.
And the truly wild part? You know. You are fully, painfully conscious that you are a woman who, just three hours ago, googled "is it normal for your lower back to make a sound like bubble wrap." You know all of this. And yet you are still over here doing the thing. The lean. The laugh. The eye contact that's just a beat too long. The flirting choreography of a twenty-two-year-old, performed by a woman whose doctor now uses the word "maintenance" like it's a lifestyle.
Maintenance. That's what they call it now. Not "getting older." Not "falling apart." Maintenance. Like you're a Honda Civic. Like someone just needs to rotate your tires and you'll be back on the road, purring.
And the maintenance is constant. There's the face maintenance. The joint maintenance. The hair maintenance. The mood maintenance, which is really just a very expensive subscription to not crying at car commercials. By the time you've assembled yourself into someone who could plausibly be flirted with, it's already 7:15 p.m. and you're at the bar because you earned it, damn it, and if Jake wants to call that "flirting," then Jake can call it whatever he wants.
The worst part? You can't even tell if you're doing it right anymore. Flirting used to be instinctive. It was effortless. It was just... existing in a way that invited attention. Now it feels like operating heavy machinery after taking Advil. You're functional. You're present. But there is a small, persistent lag between the intention and the execution.
So Jake smiles. And you smile back. And for approximately eleven seconds, you are not a person who takes magnesium supplements and has a preferred brand of knee brace. You are just a woman. At a bar. Being seen.
And then he says, "Can I get you another?" and you say, "Please," and for one gorgeous, unregulated moment, you are not a woman with a pill organizer and a strong opinion about thread count.
You are just a woman. At a bar. Being dangerous.
Then you stand up too fast and your knee pops audibly and the moment is over.
But it was a good moment.






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