So you’re looking for a new job. Maybe you’re fresh out of school. Maybe you’re burnt out. Maybe you’ve been swiping through job boards like it’s LinkedIn Tinder, and one finally caught your eye. It seems promising: competitive salary, progressive values, nice pictures of diverse people smiling on the website. But hold on. Before you get dressed up for the interview and start imagining your name on the office door, you might want to ask the question most people forget to ask:

Why is this job single in the first place? Because just like in dating, jobs break up with people (or get dumped) for a reason. And if you don’t know that reason, you might end up on a second date wondering why the last three people in your position left so fast they didn’t even bother to water the plants.

Good Reasons and Bad Reasons

Sometimes the job is single for a good reason. It’s newly created. The organization is expanding or innovating. A beloved leader got promoted and left the seat warm for the next person to shine. Like meeting someone who’s single because they’ve been focused on grad school or starting a business, that’s a green flag. Growth, momentum, potential. Other times… not so much.

Maybe the job has been “in a relationship” with five different people in three years. Maybe HR says “we’re a fast-paced environment” the way someone says “I’m a lot to handle.” Maybe the last person left with a stress rash and a locked Instagram.

In those cases, the job is single because it’s emotionally unavailable, micromanaged, toxic, or already married to someone else’s unspoken expectations.

Ask the Real Questions

In interviews, we tend to focus on impressing. But real due diligence means asking the questions that tell you what the job is actually like on the inside.

Try: “How long was the last person in this role?” “What’s the leadership style of the supervisor?” “What support systems are in place for people starting this role?” “What would success look like after six months?”

These questions are the equivalent of asking: “So… how did your last relationship end?” Because odds are, if the job ghosted someone before, it might ghost you too.

Patterns Don’t Lie

Here’s the hard truth: jobs usually break up with you for the same reason as the last person, unless something has changed. And if nothing’s changed, then you’re not stepping into an opportunity. You’re stepping into a unhealthy cycle.

Maybe the job looks shiny now, but three months in you’re being blamed for systemic failures or navigating office politics that no one told you existed. It’s like dating someone who says their ex was “crazy” — and the one before that, and the one before that. Eventually, you realize the common denominator isn’t the exes.

It’s them.

You Deserve a Job That’s Ready

Some jobs are still healing. Some are still figuring out what they want. Some want a hero or heroine to come fix everything without authority or support. And you’re not wrong for wanting clarity, kindness, structure, and growth.

You’re not too picky. You’re discerning. Because you’ve been through enough to know what you need to thrive. So next time you’re eyeing that “dream job,” pause and ask yourself:

Is this job ready for a healthy relationship? Does it come with emotional maturity (i.e., clear expectations and boundaries)? Is it offering partnership — or just performance?

Final Thought: Don’t Just Accept the Offer — Accept the Truth

Every job has a history. Every workplace has a reputation. Just like every person you date has a past — and sometimes a very messy one. That charming job offer might look great on paper, but so did your ex’s dating profile. Before you say yes, do your homework. Ask around. Read the room. Google like your sanity depends on it, because it just might.

Your job isn’t just lucky to have you, it needs to deserve you. And if you’ve ever been ghosted by an employer after a “we’re a family here” onboarding, or gaslit during performance reviews, you know exactly what I mean. Trust your gut. Trust the patterns. Trust your group chat.

And whatever you do, don’t forget to lawyer up, whether it’s for your prenup or your employment contract. Because “at-will employment” can turn into “at-will exploitation” real fast. Have someone who can translate that “we’re excited to have you” into actual legal protections, benefits, and boundaries. Remember: love is blind, but general counsel isn’t.

Because you’re not just looking for a job. You’re looking for a fit. A team that doesn’t just want your labor but values your voice. A workplace that doesn’t just tolerate your ambition but nurtures it. You deserve more than a paycheck. You deserve a mission. A place where you can grow and be inspired by the relationship, not just survive.

The best jobs? They aren’t clingy, toxic, or vague. They’re clear, confident, and ready for commitment. Just like you.

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