Understanding Your Workplace Affair: A Therapist’s Perspective

So you’re a 30-something guy working in the mailroom, and you’ve been hooking up with your boss – the divisional vice president. She’s married. She has kids. And the physical connection between you two is absolutely electric – maybe the hottest experience you’ve ever had. But despite how incredible it feels in the moment, you can’t shake this weird feeling that’s creeping in around the edges.

Welcome to one of the most complicated scenarios that brings people to Couples Counseling Chicago. Not because you’re in a traditional couple seeking help together, but because workplace affairs – especially ones with significant power imbalances – create emotional, psychological, and practical complications that most people aren’t prepared to navigate alone.

Before we dive into what you should do, let’s be brutally honest about what’s actually happening here. You’re not just having a fling with someone from your yoga class. You’re involved with someone who has direct or indirect control over your livelihood, your career trajectory, and your professional reputation. She’s also married with children, which adds layers of ethical complexity that probably contribute to that “weird feeling” you mentioned.

Let’s unpack this situation together, because pretending it’s simple isn’t doing you any favors.

Why Does This Feel So Damn Good?

Let’s start with the elephant in the bedroom: you mentioned this is the hottest experience you’ve ever had. That’s not surprising, and it doesn’t make you shallow or morally bankrupt for acknowledging it.

The Power Dynamic Creates Intensity

There’s a reason why power dynamics show up so frequently in human attraction and fantasy. When someone in a position of authority shows interest in you – someone who normally makes decisions, commands rooms, and holds influence – it activates something primal in us. It feels validating. It feels exciting. For many people, it’s genuinely arousing.

You’re a guy working in the mailroom. She’s a divisional vice president. That’s a significant gap in organizational hierarchy, and whether you consciously acknowledge it or not, that power differential is likely part of what makes this so intense. The fact that she chose you – that someone with her status and authority finds you desirable enough to take this risk – hits different than attraction from someone on your same organizational level.

The Forbidden Element Amplifies Everything

She’s married. She has kids. You both know this shouldn’t be happening. Every encounter carries risk – of getting caught, of her marriage imploding, of you losing your job, of colleagues finding out. That element of taboo and danger creates an adrenaline rush that can make every interaction feel more charged and memorable than it might otherwise be.

Neuroscience backs this up: our brains often can’t distinguish between arousal from danger and arousal from attraction. The heightened state of awareness, the secrecy, the risk-taking behavior – all of these activate the same neural pathways as sexual excitement, which is why forbidden affairs often feel more intense than relationships without these complications.

The Physical Chemistry Is Real

Look, sometimes two people just have incredible physical chemistry. That’s not diminished or invalidated by the problematic circumstances. Your body doesn’t care about organizational charts or marriage vows. If the physical connection is genuinely extraordinary, that’s a legitimate part of what’s happening here, separate from all the other factors.

So Why Do You Feel Weird?

Now let’s address that nagging feeling you can’t shake – the one that brought you here looking for answers in the first place.

Your Gut Knows This Can’t End Well

That weird feeling? It’s probably your intuition trying to get your attention. Your rational brain might be enjoying the ride, but some part of you recognizes that there’s no realistic scenario where this ends without collateral damage.

Think about the possibilities:

She stays with her husband, and you remain the secret she compartmentalizes away from her “real life”
She leaves her husband for you, and you become the guy who broke up a family (plus, you’d be starting a relationship built on deception and betrayal of others)
Someone finds out at work, and there are professional consequences for both of you – though realistically, more severe ones for you
The intensity fades, and you’re left working in a building where you have to see her regularly, navigating the awkwardness while she returns to her life

None of these are exactly storybook endings. As an aside, if you think you will be able to keep this quiet forever, think again. It almost always comes out. Even if the both of you keep your lips zipped, it still has a way of coming out.

The Power Imbalance Is Real, Even If It Feels Good

You might feel like you’re equals when you’re together, especially if she’s vulnerable or open in ways she may not be with others. But the structural reality remains: she has significantly more power than you do, both professionally and in terms of what she has to lose.

If this relationship sours, who’s more likely to face consequences? If someone needs to be moved to a different department or let go to avoid scandal, whose career is more expendable? If your work performance is questioned or you need a reference for your next job, who controls that narrative?

You might be thinking “she would never do that” – and maybe you’re right. But people do surprising things when they’re protecting their marriages, their families, their reputations, and their careers. That weird feeling might be your subconscious recognizing that you’re in a fundamentally unequal position, regardless of how she treats you in private.

You’re Complicit in Deception

Whether you’ve met her husband or not, whether you’ve seen photos of her kids, you know they exist. Every time you’re together, there’s an implicit reality that you’re participating in something that, if discovered, would cause pain to people who did nothing to deserve it.

For some people, this doesn’t bother them much – they rationalize that her marriage is her responsibility, not theirs. For others, this sits heavier. If you’re feeling weird, part of it might be a value conflict between what you’re doing and who you want to be as a person.

What People Get Wrong About Workplace Affairs

Before we talk about what you should do, let’s dispel some myths that might be clouding your judgment.

Myth: “We’re Consenting Adults”

This is technically true but fundamentally incomplete. Yes, you’re both adults making choices. But consent gets complicated when there’s a power differential. Even if you genuinely feel that you’re making a free choice, the reality is that power dynamics affect decision-making in subtle ways we’re often not consciously aware of.

Would you feel equally free to end this if you wanted to? To say no to her requests? To set boundaries without worrying about professional repercussions? If the answer to any of these is uncertain, then the “consenting adults” argument doesn’t hold up as cleanly as it might seem.

Myth: “What Happens Outside Work Doesn’t Matter”

This one gets repeated a lot, but it’s simply not true – especially when one person is in a position of authority over the other. Your relationship absolutely affects the workplace environment, even if you think you’re being discreet.

Are you getting better assignments? Are your mistakes overlooked more readily? Do you have more flexibility in your schedule? Even if none of these things are consciously happening, other employees may perceive favoritism, and their perception affects workplace dynamics whether it’s accurate or not.

Myth: “She Must Not Be Happy at Home”

Maybe she isn’t. Or maybe she is generally content but seeking something different or exciting. Contrary to popular belief, many people who engage in affairs report being reasonably satisfied in their marriages. Sometimes affairs are about escape or novelty rather than fundamental unhappiness.

The point is: you don’t really know what’s happening in her marriage, and whatever she tells you is filtered through her need to justify this relationship to herself and to you. Don’t base your decisions on assumptions about her domestic situation.

Myth: “This Is Different Because It’s Real”

Every person in every affair believes their situation is unique and special. The intensity you feel is real, but it doesn’t necessarily mean this is a sustainable or healthy foundation for anything long-term.

Strong physical chemistry combined with secrecy, risk, and power dynamics creates a potent cocktail that can feel like fate or destiny. But strip away those elements, and you might find something very different underneath. Or you might not – but you won’t know until the circumstances fundamentally change, which they would have to for this to become an actual relationship.

WTF Should You Actually Do?

Now for the hard part: making a decision about what comes next. There’s no perfect answer here, but there are more honest and less honest paths forward.

Option 1: End It Now

The cleanest option – though admittedly not the easiest – is to end this affair before it gets more complicated or someone gets seriously hurt.

Why you might choose this:

You recognize that the power imbalance creates an inherently unstable foundation
You don’t want to be complicit in deception that affects her family
You value your professional reputation and don’t want to risk it further
That weird feeling is actually your values telling you this isn’t aligned with who you want to be
You want to be available for a relationship that isn’t built on secrecy and has potential for a real future

How to actually do it:

This requires direct communication. You can’t ghost your divisional vice president – you still work in the same building. Have a private conversation where you’re honest about enjoying the connection but recognizing it needs to end. Keep it brief, kind, and firm. Don’t leave room for negotiation or “one last time” scenarios.

The aftermath will be awkward. You’ll likely need to start looking for a new job if you want to avoid the ongoing discomfort of seeing her regularly. But starting fresh without this complication might be exactly what you need.

Option 2: Keep It Going, But Get Real About What It Is

If you’re not ready to end it, at least stop lying to yourself about what this relationship actually is and what it can realistically become.

This means accepting:

You are the secondary priority in her life, and that’s unlikely to change
This relationship has an expiration date, even if you don’t know when it is
The intense physical connection might be partially fueled by circumstances that wouldn’t exist in a normal relationship
You’re taking professional and personal risks for something that probably won’t result in a long-term partnership
That weird feeling isn’t going away as long as the fundamental circumstances remain the same

Setting some boundaries might help:

Be honest with yourself about what you’re actually getting from this
Don’t put your life on hold waiting for her situation to change
Continue dating other people if you want more than just physical connection
Recognize the signs if this starts affecting your mental health or self-worth

Option 3: Have the Conversation About What She Actually Wants

If you think there might be potential for something more substantial, the only way to find out is to have an uncomfortable conversation about where she sees this going.

Ask the hard questions:

Is she planning to leave her marriage?
If so, what’s her timeline, and what steps is she actually taking toward that?
What happens if you’re discovered at work?
How would she handle it if you wanted to date other people?
What does she actually see as the future of this relationship?

Be prepared for answers you might not want to hear:

She might not have clear answers. She might get defensive or tell you you’re overthinking it. She might say she cares about you but isn’t planning to leave her marriage. Pay attention to her responses – or her avoidance of responses – because they’ll tell you what you need to know about the viability of anything beyond the current arrangement.

Option 4: Focus on Your Own Professional Development

Regardless of what you decide about the relationship, it might be time to think seriously about your career trajectory.

Working in the mailroom at 30 isn’t inherently a problem, but if you’re going to engage in risky behavior that could jeopardize your current position, you should probably be developing skills and connections that give you other options.

Consider:

What career path actually interests you?
What skills or credentials would help you move forward?
Are you staying in this job partially because of this relationship?
What would your professional life look like without this complication?

Getting clarity on your own goals – separate from her and this affair – might actually help you see this situation more clearly and make a more informed decision about what serves your best interests.

The Questions You Should Be Asking Yourself

Beyond the immediate decision of whether to continue or end this affair, there are some deeper questions worth exploring:

Why Did This Happen in the First Place?

Understanding what made you available for this relationship can be valuable, regardless of what you decide to do next. Were you feeling stuck professionally or personally? Was there something appealing about being chosen by someone in a position of power? Are there patterns in your past relationships that connect to this dynamic?

These aren’t judgmental questions – they’re opportunities for self-awareness that can help you make better choices moving forward.

What Are You Actually Getting From This?

Be honest. Beyond the physical connection, what needs is this relationship meeting? Is it:

Validation or ego gratification from being desired by someone in her position?
Excitement and intensity that’s missing from other areas of your life?
A distraction from having to face other challenges or decisions?
Genuine emotional connection that you value?
The thrill of secrecy and transgression?

None of these answers are wrong, but knowing what you’re actually seeking can help you assess whether this is the healthiest way to meet those needs.

What Does “Feeling Weird” Really Mean?

That weird feeling is information. It’s worth unpacking what specifically triggers it. Is it:

Guilt about her family?
Anxiety about professional consequences?
Recognition that you want something she can’t or won’t give you?
Intuition that you’re in a situation that doesn’t align with your values?
Fear that you’re being used or manipulated, even if subtly?

Getting specific about the source of that discomfort can help you address what’s actually bothering you rather than just living with general unease.

What Happens Next Is Your Choice

Look, nobody reading this can tell you definitively what to do. You’re going to have to sit with the discomfort of your situation and make a choice based on your own values, goals, and tolerance for various types of risk and regret.

But here’s what I can tell you from years of working with people navigating complicated relationship dynamics:

The intensity you’re feeling right now will not last forever. Whether you end this next week or continue it for another year, the heightened chemistry and excitement will eventually diminish. The question is what you’ll be left with when it does.

Power imbalances affect relationships in ways you can’t always see clearly while you’re in them. You might genuinely feel like equals, but the structural reality of her having more power than you creates dynamics that will likely become clearer in retrospect than they are right now.

Your gut instinct – that weird feeling – is probably trying to tell you something important. When we ignore our intuition repeatedly, we often end up facing exactly the consequences we were unconsciously trying to avoid.

You deserve more than being someone’s secret. Regardless of how good the physical connection is, if part of you wants something more substantial – real partnership, transparency, a future you can actually build together – this situation can’t give you that under the current circumstances.

The longer this continues, the more complicated the ending becomes. If you think this needs to end eventually, doing it sooner rather than later typically results in less overall damage to everyone involved.

A Final Word

Workplace affairs happen. People make complicated choices for complicated reasons. You’re not a terrible person for being in this situation, but you are a person with agency who gets to decide what happens next.

That weird feeling you mentioned? It’s probably worth listening to. Our bodies and our instincts often recognize what our conscious minds aren’t ready to admit: that we’re in situations that don’t serve our long-term wellbeing, even when they feel good in the short term.

Whatever you decide, make it a conscious choice rather than something that just happens to you. Own your decision – whether that’s ending it, continuing it with clear eyes about what it is, or having a direct conversation about where it’s headed.

And if you’re struggling to navigate this on your own, talking with a therapist can provide clarity and perspective that’s hard to access when you’re in the middle of an emotionally intense situation. Sometimes having a neutral third party to process this with can help you see what you actually want more clearly.

You asked WTF you should do. The honest answer is: whatever you can live with when you look back on this situation five years from now. Make that choice intentionally, not by default.

Need Support?

If you’re struggling to navigate workplace dynamics, complicated relationship situations, or decisions about what you truly want in your personal and professional life, Couples Counseling Chicago is here to help. While we specialize in couples therapy, we also work with individuals navigating complex relationship dynamics and life decisions.

We provide a safe, non-judgmental space where you can explore your situation honestly and make decisions that align with your values and goals. Contact us today to schedule a consultation.

I’m Sleeping With My Boss But Feel Weird

Understanding Your Workplace Affair: A Therapist’s Perspective