Dating In The Workplace: A Career Portfolio Asset For Women?
- Cassie Wilson
- Jan 22
- 2 min read
Updated: Jan 24

In recent entertainment news there’s been a ton of talk around “inappropriate” relationships in the workplace. More specifically, relationships of a romantic nature that may or may not lead to career advancements for women. Before I rub my hands together and dig in, here’s a little disclaimer:
There’s a fine line between sleeping your way to the top and leveraging your relationships
If you’re a talent-free or lazy person - I would 2000% tell you, “abort mission - do not sleep with your superiors in hopes of career advancements, no matter what you think”… thinking isn’t your strong-suit (respectfully)
I DO NOT believe in a flagrant tradeoff between sex and career opportunities*
Despite all of that, I fully support women who can identify an opportunity that has the potential to work in their favour.
Dating strategically in your career is like diversifying your investment portfolio.
Shocking? Maybe.
Risky? Yup.
Smart? Only if you are.
The Investment Strategy Breakdown
Just like you wouldn't put all your money into one risky stock, your career advancement shouldn't depend solely on one thing. Strategic dating can be part of your portfolio - but it's never the whole game, baby.
Your talent and skills are your blue-chip stocks - your foundation
Strategic relationships are your high-risk, high-reward investments
Making it Crystal Clear
This isn't about manipulation. It's about mutual benefit. Here's what you need to know:
Always bring real value to the table - your skills must be top-notch and a baseline of respect from both parties is absolutely necessary**
Know your exit strategy before you enter (just like any other smart investment)
Keep your professional reputation spotless - discretion is non-negotiable (BUT be prepared for shit to blow up at any given time)
Have clear boundaries and stick to them - don’t forget to communicate any boundaries that need to be communicated. As far as personal boundaries go, you can keep those cards close to your chest, but be sure to reference them regularly - never forget your black bottom line
Your Risk Assessment:
Not everyone should play this game. Like any high-stakes investment, you need:
Emotional intelligence and problem solving abilities off the charts
A solid backup plan (always!)
The ability to handle potential fallouts and a PR crisis
A clear career trajectory and northern star
Here's the mic drop: this entire concept isn't that different from nepotism, traditional networking, or any other relationship-based advantage. It's just more taboo to talk about. Your career and life is yours to build. Use every advantage wisely, and try your best to make decisions that seamlessly align with your morals and beliefs.
Note to reader: It’s so damn important to critically think about these concepts and make decisions based on your own beliefs. There is no right, there is no wrong, there just is.
*I do, however believe in an exchange of cold, hard cash … then sleep with that man if you choose to
** you know when people don’t actually value/respect/fuck with you
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