From Bad Dates to Bad Deals: 5 Tips to Win in Love and Business
Single, dating, married, in a situationship? Running a business, working for someone, or just brainstorming your next big idea? Whatever your personal or professional status, I’ve got five game-changing tips that apply to both dating and business. And let’s be honest, they’re basically the same thing—both involve strategy, negotiation, and the occasional disaster.
So, let’s get into it.
NUMBER 5: UNDER PROMISE AND OVER DELIVER
Ah, the classic bait-and-switch. I will never understand why people put decade-old or 10kg-lighter photos on their dating profiles. Do they not realise the entire point of online dating is to eventually meet in real life?
Case in point: I once went on a date with a guy who looked NOTHING like his profile. When I arrived, I genuinely walked straight past him in the bar.
Same goes for business—don’t catfish your clients. Don’t promise them the world and then deliver a sad PowerPoint. Nothing kills a reputation faster than over-promising and under-delivering. I’ve been so excited to work with certain people, only to be let down when they didn’t follow through.
You know what’s better? Exceeding expectations. I want people to think, “Oh, I thought she was good, but wow—she was GREAT.” In dating, when I walk toward my date (hair toss, check my nails), I want him to do a double take, flash a grin, and think, 'Damn, I hit the jackpot.' A little dramatic? Maybe. But hey, first impressions count!
NUMBER 4: START SLOW
Never commit to a dinner for a first date. Rookie mistake. That’s at least two hours with a total stranger, and trust me, that can feel like a lifetime.
Take it from me—I once had a marathon first date: pre-dinner drinks at bar called Loose Moose, dinner at Social restaurant, cocktails at Moo Moos. That’s five hours of my life I will never get back.
The business equivalent? Diving headfirst into a massive project with a brand-new client before even figuring out if you’re a good fit. Start with a coffee chat, a quick consultation, or a small pilot project before committing long-term. It’ll save you a lot of headaches (and, in dating, the need for a well-timed "emergency call").
NUMBER 3: FOLLOW YOUR INTUITION
You know that indescribable something you feel when you meet the right person? It’s the same in business.
I want to feel that chemistry when I go on a date. Same in business. I once walked into a client’s office, met their executive team, and from the get-go, something felt off. I ignored my gut, took the project anyway, and—surprise, surprise—it didn’t work out.
Lesson learned: If there’s no chemistry, whether in dating or business, don’t force it.
NUMBER 2: BE YOURSELF
Authenticity is everything.
Look, I’m 50 years old—no more faking it. I could go on a date and act all shy, coy, and demure. But honestly? It sounds exhausting. I'd rather just wear a T-shirt that says #TOOMUCH and let them decide upfront.
Same goes for business. Not everyone is going to want to work with you, and that’s a good thing. You can’t be everything to everyone. Instead, own your strengths, lean into what makes you unique, and the right people—whether dates or clients—will find you.
AND FINALLY, MY NUMBER 1 TIP: KEEP IT FUN!
If dating isn’t fun, if business isn’t fun, you’re doing it wrong.
I get it—outcomes matter. In dating, you might be looking for a long-term partner. In business, you're aiming for serious results. But that doesn’t mean you have to be serious all the time.
When you keep things light, you naturally bring out qualities like kindness, generosity, and gratitude. And guess what? Those are very attractive—whether you're closing deals or closing the distance on a great first date.
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This Valentine’s Day, I’ll be snuggled up with my boyfriend. But before meeting him, I spent years in the dating trenches—ahhh, the memories (and the therapy bills). And I’ve been in business just as long. If there’s one thing I’ve learned, it’s that dating and business have way more in common than we think. So, whether you’re negotiating contracts or planning a date, take a deep breath, trust your instincts, and most importantly—have fun!
I’m Midja. You’ll find me on LinkedIn, Instagram, and, thankfully, no longer on dating apps. 😉