If you’ve ever rushed from a back-to-back Zoom marathon, touched up your mascara in the Uber, and prayed your date wasn’t another LinkedIn bro in disguise… girl, this one’s for you.
Being a boss in the boardroom and a babe at happy hour is no small feat. But dating while juggling a demanding career? That’s a full-time job with zero PTO.
So before you invest another perfectly good outfit and three hours of your evening on a lukewarm cocktail and a “crypto enthusiast,” let’s talk about the six first date mistakes you do not need to make anymore, and how to dodge them like the queen you are.
1. Showing Up in “Interview Mode”
The Mistake:
You’re so used to leading meetings, pitching ideas, and powering through client calls that you accidentally turn your date into a performance review. (Complete with nervous laughter and way too many resume references.)
The Fix:
Breathe. You’re not here to impress, you’re here to connect. Ditch the polished pitch and let a little of your quirky, off-duty self show. Share the story of how you accidentally called your boss “babe” instead of “Bob.” (It happens. We survive.)
Real Talk: He’s not hiring. He’s hoping you’re not a catfish.
2. Overbooking Your Calendar (and Yourself)
The Mistake:
You squeeze a date in between your spin class and your Q2 report like it’s just another task to tick off.
The Fix:
Carve out actual space. Emotionally and physically. Give yourself an hour before to reset, vibe, and mentally change gears. Light a candle. Play your “Hot Girl Energy” playlist. Whatever gets you in your zone.
Pro Tip: You deserve dates that feel like you time, not overtime.
3. Pretending You’re Less Ambitious Than You Are
The Mistake:
You downplay your title, your salary, your TED Talk, because you’ve learned some men can’t handle a woman who doesn’t shrink herself.
The Fix:
No more minimizing. If your ambition scares him, that’s a “him” problem. Lead with your light. The right one will be dazzled, not diminished.
Mic Drop: You’re not “too much.” You’re just not for people who want too little.
4. Going In Without Any Intentions
The Mistake:
You say, “I’m just seeing where things go,” but deep down you know you’re craving connection, not just someone to split a bottle of Pinot with on Thursdays.
The Fix:
Know your why before you swipe. Are you dating for fun, for future, or just for free dessert? All valid. But be honest, with yourself first. It’ll save you from unnecessary emotional detours.
Power Move: Clarity is confidence. Don’t let vibes lead where values should.
5. Ignoring Red Flags Because “He’s Cute and Has a Job”
The Mistake:
He talks over the waiter, lowkey disses his ex, and forgets your name halfway through, but he owns property, so you let it slide.
The Fix:
Raise your standards and your eyebrows. You don’t need perfection, but basic decency is non-negotiable. No more mistaking potential for partnership.
New Rule: If the bare minimum feels like a win, it’s time to rewrite the scoreboard.
6. Forgetting to Enjoy Yourself
The Mistake:
You’re so focused on the “what ifs”, What if he ghosts? What if this is a waste of time?, you forget to be present. To actually have fun.
The Fix:
Reclaim your joy. Laugh too loud. Order the fries. Flirt like you’re 22 again but with 10x the self-worth. Whether or not he’s “The One,” the night should still feel worth it.
Mood: You’re not just the date. You’re the main character.
Because here’s the deal,
You’re not just a working woman. You’re a whole woman. Brilliant, busy, badass, and absolutely deserving of a dating life that reflects that.
So the next time you’re out there, remember: you don’t need to shrink, stretch, or stress to be loved. You just need to show up as you.
Now spill it, what’s your most cringe first date story? Drop it in the comments and let’s laugh/cry together. We’ve all been there.