• It’s important to know for sure that your boss is into you before making a move
  • Look out for signs that they treat you differently from others
  • Either tell them to back off or get ready for a workplace romance
Did he just wink at me or does he have something in his eye?

Was that a bit of flirtation or is she this friendly with everyone?

Is she inviting me for after work drinks or has everyone received this same invitation?

One of the hardest things about dating is knowing whether or not someone is actually into you or not.

Add a corporate setting and this is even more tough to figure out.

At work, people are less likely to be forward and probably more fearful of the repercussions if the feeling isn’t mutual. So, knowing whether your colleague has the hots for you can take longer than it would in a social setting.

But what if your potential love interest is your boss?

Well, the first and most obvious thing here is that if you or your boss are married, you need to shoot this down asap. Having an affair at work will be nothing but a big fucking disaster.

Put simply, don’t do it.

However, if the both of you are single or divorced, you definitely want to be sure you’ve read the signs correctly before making any moves with that.

Not only would crossed wires in this situation be embarrassing, it could actually affect your career and personal brand.

So, if you think your unmarried boss might have the hots for you, what exactly are you supposed to do about it?

First, you’ve gotta be sure.

Then, there are some simple steps you can take to let them know if the feeling is mutual and start moving towards an office romance or keeping your distance if it’s not.

But First, Dating At Work

We seem to make a big deal out of it but dating at work is actually very normal. Lots of people, maybe even friends you know, have dipped their pen in company ink.

We spend a third of our lives at work, in close proximity with the same people day in and day out.

A lot of the time, we’ll be in close quarters with people from similar age groups, backgrounds and with at least some similar interests with us.

All of this makes the workplace ripe for at least some office romances.

This survey from Society for Human Resource Management found that 54% of American workers had a crush on a coworker, 41% were brave enough to ask a coworker out on a date and 27% of people had a full-blown office romance.

So dating at work is kind of a given. But what about dating your boss?

Obviously, the whole dynamic changes when the budding romance is taking place across hierarchical lines but that’s not to say that it can’t work. It’s just that shit just gets a little complicated.

In the same survey mentioned above, 27% of those who dated at work did so with a higher up. Whether or not it got them the promotion or bonus is unknown. 😉

Sure, there are certain things to consider and a lot more risk involved in dating your boss. But there are plenty of people who have done it successfully.

But wait! We hear you scream.

I don’t even know for sure if my boss is into me yet! Or if I’m really that into them.

Before you start fantasizing about your destination wedding with your boss, you need to make sure that you’re reading the signs correctly and be clear about your own emotions.

Does Your Boss Have The Hots For You?

We wish we could give you a simple yes or no quiz that would answer this question with absolute certainty but nothing is ever that easy.

The truth is, sometimes we might think someone is into us when actually they’re just a very flirty, outgoing person.

Other times, the person might have taken a genuine liking to us but only platonically.

It can be quite difficult to figure things out. The important thing is to give it time. It’s not a good idea to jump to conclusions about your manager’s feelings for you after one day. They might have just been in a really good mood!

Once you start to notice the signs, give it a good few weeks or even months and see if the signs remain consistent and exclusive to you. If they do, then you can move forward with relative confidence that they have feelings for you.

But what exactly are the signs?

You might think the obvious sign is flirting but you’ll notice that it’s missing from our list.

This is because flirting is so fucking vague!

First of all, people flirt in different ways. Second of all, some people flirt just because - not because they like you in that way. And finally, flirting isn’t tangible enough. It leaves you wondering, “are they flirting? Or am I imagining things?”

So, here are the more obvious signs that someone is crushing on you.

1. Being Overly Helpful

Your manager is supposed to help you. They are there to support you in your continued growth and development. But is your boss being overly helpful?

Perhaps they seem almost as if they want to do your work for you. Or maybe they are overprotective, shielding you from asshole coworkers, tough tasks and scary senior management.

Although this might actually be quite annoying as it could stunt your growth and leave you feeling stuck in your career, your boss likely thinks they’re being your knight or knightess in shining armor. And if Disney has taught us anything, it’s that you always fall in love with the one who saves you!

2. Dishing Out Lots Of Compliments

We’re all trying to make good bonds at work. And that often involves paying a few compliments here and there occasionally. So how can you tell if these compliments are coming from someone who’d like to get past the friend zone?

First, notice the type of compliment.

If your manager is complimenting the formatting of your spreadsheets, they probably just think you’re great at your job. But if they’re complimenting your clothes, your appearance, your personal qualities, then maybe they’re more interested in your suitability as a lover.

Second, you can tell a lot from the way in which the compliment is delivered.

Do they speak shyly, maybe even blushing or looking away? This is definitely a sign that they’re into you.

3. Giving Special Gifts

Everyone loves receiving prezzies, right?

Now, we’re not saying you should expect your boss to buy you cars and take you on exotic vacations if they really want to win your heart. Hopefully, they’re a bit more subtle than that.

A photo frame for your desk, a special pen, a cubicle desk plant, a pretty notebook - these kinds of gifts might seem like friendly gestures. But, if they are thoughtful and have some sentimentality behind them, these could be signs that your manager has feelings for you.

If you’ve received any gifts from your boss, take a look at the items and see if any of them have a story behind it. If so, you might be looking at the gifts of a not-so-secret admirer.

4. Making Eye Contact

Do you catch your boss staring at you? Do you feel butterflies when you lock eyes? Or do you feel creeped out?

They say the eyes are the window to the soul, so you may be able to decipher your boss’s true feelings just from looking at them.

Next time you lock eyes, instead of averting your gaze quickly, let it linger for a moment and see what you find and how you feel.

It’s also a nice little break from all the digital eye strain from staring at the monitor.

5. Physical Contact

It is important to note here that any inappropriate physical contact or any other behavior that makes you uncomfortable is unacceptable and should be reported to HR asap.

If, however, your boss is respectful and wants to make their feelings for you known, you will likely notice it in behaviors like: standing close to you, placing a hand on your back, arm or shoulder, hugging as a greeting, allowing their hands to linger a little on a handshake, etc.

You will notice that, generally, their body language towards you is very open and warm.

Or, they may just blatantly cross the line like Dale’s crazy-ass lady-boss in the movie Horrible Bosses.

VIDEO: Crossing the line
YOUTUBE: Akillheals
LENGTH: 2:20

6. One-on-One Time

Every manager and subordinate has to spend some one on one time together. But when your boss is into you, you might see the frequency of this alone time going up.

You might find yourself in one-on-one meetings that could definitely have been replaced by a simple email or desk-side catch up. Or, maybe the end of day meeting might extend into the early evening with an offer for dinner.

Whether they are doing it consciously or not, your boss is trying to get some alone time with you because they enjoy your company. The question is, do you enjoy theirs?

7. After Hours Contact

Taking the point above further, your admirer might also want to get some time with you away from the office. This one’s a dead giveaway.

As we know, getting out of the office helps us connect with colleagues on a more personal level, so what better way to allow a potential romance to blossom?

Your manager might invite you out for dinner or drinks, or they may suddenly take a huge interest in whether or not you are planning to attend work social events like office happy hours - just be sure to follow happy hour etiquette.

8. Valuing Your Opinion

When we are romantically drawn to someone, their opinion matters to us. Do you find your boss asking your opinion on things that don’t fall under your responsibilities? Or maybe they are even coming to you for advice on personal matters.

These are signs that they highly value your opinion, which could mean they want to be more than friends.

However, be sure to push back if you feel uncomfortable with any of the conversations. For example, your boss shouldn’t be asking you about your opinions on sex life and dating preferences.

9. Treating You Differently

None of the signs above really mean anything if you notice your boss acting exactly the same way with everyone else.

Ultimately, the sure sign that your manager is into you is that they treat you differently from other coworkers, in a better way. It’s the exact opposite of an asshole boss. It’s preferential treatment.

So, be on the lookout for how they interact with others in the office and let this be your baseline measurement. And, if you see that they are treating you in a much better way, that’s a clear sign that they’re into you.

10. Follow Your Gut Intuition

Despite all our umming and ahhing, we usually just know when someone has a crush on us. If you have an inkling that your boss wants to get in your pants, you’re probably right.

But taking time to look out for these signs can help you be absolutely sure before you do anything about it.

And once you are sure, what’s next?

Should You Date Your Boss?

The most important step after realizing that your boss has the hots for you is deciding on how you feel.

Because of the power dynamic, it could be easy for you to think you also like them, when really all that’s at play is an imbalance in power.

Ask yourself, “how did I feel about them before I realized how they felt about me? Would I still be into them if they were my direct report?”

These questions should help you get to the truth of your feelings.

If you decide you don’t feel the same way, it’s time to nip things in the bud. Be very clear in your speech and actions to let them know you’re not into them. This can be subtle at first; declining unnecessary meetings, saying no to dinner, not accepting gifts, etc.

If they don’t get the message, then you’ll have to be blunt and direct. Sit them down and let them know you’re uncomfortable with the advances and you would like to keep the relationship strictly professional.

If that doesn’t work, then you’ll need to get HR involved. Reach out to them and explain the situation and ask that they take action on it.

If you do feel the same way, however, then this is the fun part. It’s the start of a budding romance. Dating your boss can be a minefield so just make sure you take the following tips into account.

  • Be clear on your feelings
  • Ensure that it’s mutual
  • Check your workplace policy
  • Assess the risk / reward
  • Think about what will happen if it doesn’t work out
  • Be honest and open
  • Keep healthy boundaries
  • Forget your priorities
  • Be secretive
  • Bring work matters into your relationship
  • Abuse your relationship for personal gain
  • Gossip
  • Abuse company expenses
  • Date married men/women
Dating your boss can be a wonderful thing. You just have to be smart about it to avoid disaster and the office gossip trap.

It’s Time To Scope Things Out

While all this cat and mouse business can be quite alluring, at a certain point, you just want to know for sure whether someone is into you or not.

Unfortunately, we don’t live in a world where you can just walk up to them and say "So, are you crushing on me?" - especially when that person is your boss.

But with a little bit of detective work and a lot of observation, you can be pretty sure of where you stand.

Knowing that you have an admirer at work can add a bit of excitement to your day, and could be the start of a beautiful workplace romance. If that’s something you’re open to or want.

And if it’s not, then you’ll have a lot more clarity in how to put the kibosh on things. It’s all part of managing your boss.

Either way, you’re in control and you can shape how things turn out.

Feel Better,

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