F*ck Fails: When Guys Screw Up & How to Avoid Their Blunders So You Can Actually Get Laid by the Bartender

It was a chilly evening in San Francisco last night, and I’d just found a cozy spot at a dimly lit bar near Union Square. The kind of place where the drinks are strong, and the people-watching is even stronger. I was nursing a whiskey sour, just minding my own business, when I noticed a guy at the other end of the bar trying to strike up a conversation with the bartender.

He was fumbling — badly. You know the type: leaning in a little too close, trying to force a cool smile, and dropping awkward lines that seemed like they’d been recycled from a bad rom-com. The bartender, bless her, was politely smiling, but you could tell she was mentally counting down the minutes until her shift ended.

And that’s when it hit me — this guy was treating the whole situation like a job interview, trying way too hard to make an impression. But the truth is, getting someone’s attention isn’t about impressing them. It’s about making them feel comfortable, seen, and understood.

Here’s the thing: whether you’re at a bar in San Francisco trying to flirt with a bartender, or at a networking event trying to make new connections, the principles are the same. And if you can master them, you’ll find that connecting with people — any people — gets a whole lot easier.

Lesson #1: Become the Host, Even When You’re the Guest As I sat there, sipping my drink and watching this guy struggle, I wanted to whisper in his ear: “Dude, chill.” You see, the most popular person at any gathering, whether it’s a bar, a party, or a networking event, is usually the host. Why? Because they’re not there to impress anyone — they’re there to make sure everyone else is comfortable.

Now, I’m not saying you need to run the bar (although that would be pretty cool). But you can bring that same energy wherever you go. Walk in, greet the bartender like an old friend, chat casually with the person next to you. When you act like you belong, people will naturally be drawn to you.

Lesson #2: Tell Stories, Don’t Give Pitches The guy at the bar made another classic mistake: he started with an awkward compliment, and then dove straight into a rambling story about his job. No one cares that you work in tech or investments or whatever the fuck you’re doing, dude — not right now, anyway. What they care about is whether you’re interesting and fun to talk to.

Especially Not for Female Bartenders: They Really Don’t Give a F*ck

So, here’s the pro tip: if you’re trying to get someone’s attention, skip the small talk and tell a story. Share a funny anecdote, something that makes people laugh, or even a surprising fact about yourself. Stories are engaging, relatable, and way more memorable than, “So, what do you do?”

Lesson #3: Listen More Than You Speak By this point, I was half tempted to order another drink just to see how this would play out. But then it hit me — the real secret sauce to connection isn’t about what you say. It’s about how well you listen.

Most people think they need to be talking to hold someone’s attention. But the best conversationalists — the ones who get phone numbers, job offers, and second dates — are the ones who ask questions, nod at the right moments, and genuinely listen.

The next time you find yourself trying to make a connection, don’t focus on impressing them. Focus on making them feel heard. Trust me, they’ll remember it long after the conversation is over.

Now I watched this poor guy swing and miss for about twenty minutes before he finally gave up and paid his tab. And I’ll admit, there was a part of me that wanted to go over and give him a quick lesson on how to do it right. But hey, you’ve got to admire the guy’s guts.

Here’s the deal, though: making a connection isn’t just about having the right lines. It’s about who you are and how you present yourself. You can walk into any room, in any city — including a San Francisco bar — and be that person people want to talk to. You just need to relax, be present, and let the conversation flow naturally.

So, next time you’re out there, don’t try so hard. Just be yourself, have a good time, and see where it leads. Who knows, you might just end up with more than a phone number — you might make a real connection.

And in a moment, I’ll tell you about banging this old guy who annoyed the hell out of me and managed to offend me — which is saying something, considering I fuck for sport. It’s all just fuel for the stories I write to you.