Office Romance: A Cautious Guide for Modern Relationships

The following reflections are inspired by an excerpt from Liz Plank’s book For the Love of Men, in which she outlines thoughtful guidelines for maintaining a healthy workplace culture, cultivating emotional safety among colleagues, and still acknowledging the reality that attraction sometimes happens at work. Plank’s perspective offers a balanced approach; she does not insist that people avoid dating coworkers entirely, but she emphasizes the importance of navigating workplace relationships with intention, maturity, and boundaries.

That said, I want to highlight an important caveat. In general, dating within the workplace carries significant risk. If a relationship becomes strained, imbalanced, or high-conflict, the fallout does not stay contained; it spills into the work environment, creates discomfort for colleagues, and can even jeopardize professional stability. For that reason, my personal rule of thumb is to avoid workplace romances whenever possible. The potential consequences such as awkwardness or divided loyalties are rarely worth the gamble.

At the same time, I recognize the complexity of real life. For many people, the workplace is the only social environment they consistently spend time in. It is a space where trust, familiarity, and shared purpose naturally grow. Genuine connection can happen there, sometimes in ways that feel rare and meaningful. And it is unrealistic and perhaps unfair to pretend that adults never form romantic interest in the people they work alongside every day.

So if you choose to take that risk, and you believe the connection is strong enough to justify navigating the complications, then I recommend grounding your decision in Liz Plank’s guidelines. Her recommendations offer an approach that protects not only your professional reputation but also the emotional safety of the people around you. They emphasize respect, transparency, boundaries, and a commitment to preserving a healthy professional environment even when romantic feelings enter the picture.

Workplace dating is not automatically a mistake, but it is a responsibility. And if you decide to pursue it, doing so with intention and self-awareness is essential.

Here is an excerpt of  the rules verbatim from the book: 

RULE 1: TAKE STOCK OF HOW MUCH POWER YOU HAVE 

Do you know who almost always knows exactly how much or little power they have in the workplace? Women. Women, especially those of color, know exactly where they stand in the power structure because they are so often at the bottom of it. But one thing that I came across in my conversations with men was that they had often been told to check their privilege, but they have rarely been told to examine their power. Checking your privilege is passive—it often means taking a step back. But examining your power is active. I’m an advocate of the latter more than the former. I think it’s more important to take stock of how much you have and then use all of yourself for good. Also, while privilege is fixed (it’s based on fixed identities: being white, male, able-bodied), power is relational. It changes depending on situations and the people you are associating with. For instance, in the midst of the #MeToo headlines a male friend confided in me that he didn’t understand why a female coworker had felt uncomfortable about a romantic encounter they had shared. He didn’t understand why she described it as making her uneasy when at the time she didn’t protest it. When I asked him more about this woman, I realized this wasn’t just a coworker. “I’ve helped her with opportunities in developing her career,” he told me nonchalantly. “So you’re more of a mentor she relies on for advancement?” I said. He nodded yes. The more I asked questions, the more I realized he wasn’t just a friend or coworker to this woman, but that there was a clear power difference between the two of them. When I asked him if he had ever thought about the fact that he had more power in that relationship, it’s like a lightbulb went off in his head. Because men still hold the vast majority of positions of power and authority in our society, that gendered power dynamic is so frequent it’s often invisible to them. But very rarely is it invisible to the women. Power is like social mobility: the people who know the most about it often have very little of it. Because my friend hadn’t acknowledged the power dynamic between them, he hadn’t been able to see how she may not have been able to say no to his advances. It hadn’t occurred to him at the time, but given that the floodgates have now been opened, men are held accountable and have a real interest in not screwing up with them.

RULE 2: WHEN TRYING TO DATE A WOMAN AT WORK, USE THE RULE OF ONE

 In a post-#MeToo world, a lot of men are worried this is the end of office romances. As a person who has been smitten with a coworker more times than I’d like to admit, I don’t think it needs to be. In fact, almost half of people have at one point dated someone they work with and a third of those relationships ended up in marriage. Women being actually believed when they report sexual harassment didn’t ruin romance; in fact, it reset the rules of romance for the better. If you want to make sure you don’t cross the line, follow the official policy that was instituted at Facebook and Google: you only get one shot. Office romances are allowed as long as there’s no conflict of interest and a coworker only asks another once. If the answer is ambiguous (“I’m busy,” or “Maybe … let me check”) or is a full-on “No,” the person is no longer allowed to ask. Dating at work is simple: you only get one shot. 

RULE 3: BE AWARE THAT IF THE ATTRACTION IS MUTUAL IT’S NOT HARASSMENT 

Many men complain about not knowing if a flirtation will be taken as harassment. But here’s the thing: if you’re not sure if you’re flirting or harassing, you’re probably not flirting. Buddhism teaches us about conscious eating, conscious walking, and I think men need a practice of conscious flirting, especially in a work setting. Many men go into flirting with a woman as conquest, like she’s a mountain they’re trying to climb. But if they only approached flirting by putting her first, they would be able to tell right away if she was interested. The subtle cues are key and paying attention to them is even more important in the workplace since you’re both stuck there if things don’t work out. 

RULE 4: YOU DON’T HAVE TO AVOID WOMEN: JUST STOP HARASSING THEM! 

I’ve spoken to a lot of men (and women) who say they’re afraid of hiring women now. Not hiring women to solve workplace harassment is like tackling the extinction of the sea turtles by killing the ones who are left. Refusing to be in the same room as a woman after dark doesn’t exactly accomplish ending sexual harassment. It’s discrimination. Women are not the problem. The men harassing them are.

RULE 5: WHEN IT COMES TO CHIVALRY IN THE WORKPLACE, ASK IF YOU’RE NOT ABLE TO TELL 

Men should approach acts of chivalry in the workplace with a simple rule: definitely ask if you can’t tell (what’s appropriate). Ask if she needs help, but never assume she does. Beattuned to a woman’s reaction when you offer up an act of chivalry. For instance, I once had a coworker who insisted on holding my bags constantly, even after I would tell him I didn’t need help. He wouldn’t just require that he handle large bags (which honestly could have been at least useful) but would insist on carrying even the smallest handbag, making me feel like he thought I was inept because of my frail lady bones. That’s not chivalry; it’s patronizy (yes, I made that word up). If a woman says no to an act of chivalry in the workplace, believe her. On the flip side, I once worked with a producer who wouldn’t offer to help me with anything. He would just watch me struggle and it was just as annoying. Now I know this sounds like men are damned if they do, damned if they don’t, but generally as a rule, one should never operate in extremes. It’s really hard to offend someone by offering help. In fact, it’s the lack of attention to the answer that usually causes problems. As my friend’s highly mature 9-year-old daughter told me when I asked her if men should open doors for their female boss, “I have nothing against polite people.” And what goes an even longer way and literally cannot backfire is offering to do traditionally female jobs for women in the workplace, like taking notes or doing administrative tasks. Even if you weren’t in a position to take the food order or keep the minutes of a meeting, giving a woman a nod for doing it signals an appreciation for her time and work and a recognition that those are laborious tasks, too, even if often performed by women without acknowledgment. Opening the door for your female boss is nice, but booking the conference room so she doesn’t have to is even better. And there are some acts of chivalry that have a place in the dating world but no place at work. My friend Regina is an executive at a prominent media company and laments the way she is greeted differently from her male peers by collaborators. While men usually get a handshake, she often gets a hug. At one video shoot she was conducting, she reached out to the subject they were interviewing with a handshake and he ignored her hand while extending his arms to embrace her. “I’m sorry, I just can’t shake a woman’s hand,” he quipped. This is where chivalry can go too far. Women don’t want to be treated differently; they want to be treated equally. Don’t hug the women you work with unless you are hugging the men you work with. But how does one know which acts of chivalry should stay in the dating world and not migrate to the work world? This brings me to the next rule.

RULE 6: DON’T DO ANYTHING FOR A WOMAN THAT YOU WOULDN’T ALSO DO FOR A MAN 

Would you hold the door open for a man? Absolutely. Would you hug him and say you just can’t shake men’s hands? Absolutely not. If you wouldn’t do it for a man, then you probably shouldn’t do it to a woman. That’s the only gut check you need. Pretend like people don’t have genders. Don’t assume they can do less or more based on any part of their identity for that matter. People think that taking identity into consideration means treating people differently, but what it really means is treating everyone equally.