5 First Dates That Screamed “Never Again”

Ladies, ever been on a date so awkward, you mentally drafted your resignation letter from romance? Yeah. Same.

When you’re a career-driven woman with a calendar tighter than your skinny jeans post-brunch, the last thing you need is to waste your precious Thursday night on a walking red flag disguised as a “nice guy.” Whether you’re swiping through dating apps between Zoom calls or being set up by that one overly optimistic coworker, dating can feel like a second (unpaid) job.

So let’s talk about five first dates that made us want to ghost humanity ,  and how you can spot (or survive) them without losing your mind, mascara, or momentum.

1. The “I Forgot My Wallet” Guy 

Also known as: The Financial Houdini.

You’re sitting across from him, sipping a $17 cocktail after a 10-hour workday, when he drops the infamous line:
“Oh shoot, I think I left my wallet in my other pants.”

Sis… you’re not a bank, you’re a boss.

The Real Problem: This isn’t about money ,  it’s about maturity. If he’s not responsible enough to bring his wallet to a date, how’s he handling literally anything else?

The Fix: If this happens once and he Venmos you before dessert hits the table? Maybe. If not? Politely excuse yourself, pay your half, and walk away with your head high and standards higher.

2. The “Let Me Tell You Why Your Job Is Silly” Guy 

He’s got opinions about your career… and he’s not shy about them.

“You work in marketing? Isn’t that just, like, making ads all day?”
Cue the internal screaming and your soul slowly exiting your body.

The Real Problem: Some men still feel threatened by ambitious women. That’s his insecurity, not your issue.

The Fix: Shut it down. Confidently respond with, “Well, I love what I do ,  and I’m damn good at it.” If he’s not clapping for your wins, he doesn’t deserve a seat at your table (or a second date).

3. The Therapist-Seeker 

You wanted sparkling conversation. He brought emotional baggage and unpacked it all over your pasta.

“Oh wow, I haven’t talked to anyone about this since my ex left with my dog and my soul.”

The Real Problem: You’re not his therapist. You’re not even his. First dates aren’t trauma dumps.

The Fix: Compassion is cool, but boundaries are queen. If the convo goes from flirty to 50 Shades of Sad real quick, gently redirect or ,  if needed ,  cut the night short with grace. You’ve got deadlines and dignity.

4. The Mansplainer 

“Let me explain that to you…” ,  about a topic you have a degree, certification, and four awards in.

You’re halfway through discussing your latest project launch when he interrupts to explain how marketing really works. (Even though he sells printers.)

The Real Problem: He’s not listening. He’s lecturing. That’s not a partnership ,  that’s a TED Talk you didn’t ask for.

The Fix: Call it out with a smile: “That’s cute. But I’ve actually been leading that campaign for six months.” Watch his face do the mental math. Then finish your wine. Powerfully.

5. The “Let’s Keep This Casual” Bro 

It’s not even dessert yet and he’s dropping lines like: “I’m just going with the flow right now.”

Translation? He’s not looking for a relationship. He’s looking for convenience.

The Real Problem: You’re juggling a career, a gym membership you haven’t used in weeks, and your sanity ,  you don’t need to add guessing his intentions to the list.

The Fix: Be upfront about what you want. If he’s not on the same page, thank him for the drinks and move on. Clarity is hot. Confusion is exhausting.

Final Thoughts:

Dating while working full-time isn’t for the weak ,  it’s for the woke, witty, and wildly deserving. You’re building empires and still finding time to swipe right? Queen behavior. 

So next time a date screams “never again,” remember: you’re not hard to love. You’re just not for the weak-hearted or the wallet-less.

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