How To Flirt With Your Boss – Romance At Workplace

Written By Shahzaib Arshad

Respecting your boss is a good thing, but liking your boss is totally a different thing.

There can be various reasons why you might want to flirt with your boss. Maybe you’re naturally attracted to your boss and want to begin a relationship.

12 Tips On How To Flirt With Your Boss

Or maybe because you read somewhere that women who flirt have chances to proceed at work.

Whatever the reason is, it’s essential to know that flirting at work is riskier. It needs to get handled with care. we are going to cover all the aspects about how to flirt with my boss.

This article throws light on the potential risks and gives some amazing tips to flirt with your boss.

1. Do You Really Wanna Date Or Is It Boredom?:

You have opened up an article on how to flirt with boss. So are you really into this? What made you think in this way?

Are you bored? Or do you like your boss and think that flirting can turn into a real relationship.

Is that you trying to get favour at the workplace? When you rethink your motivations, you’ll be clear whether to take this risk or not.

Think Once Again Why You Want To Flirt With Your Boss
Do You Really Wanna Date Or Is It Boredom?

If you flirt with your boss, you might get that assignment you really wanted to work on.

Or you might get a desirable change in your shift. But sometimes, it can backlash depending upon the nature of the workplace. So beware!

2. How To Flirt With Your Boss – Try Not To Cross The Boundary:

Whatever your motivations are, always try to stay in your limits. 

If you’re really into your boss and look forward to begin a relationship, you must take steps with care.

Remember You Have Limits As An Employee
How To Flirt With Your Boss – Try Not To Cross The Boundary

Review your limits and never offer more than you want to provide. You don’t want to lead someone into a relationship you never wanted.

3. Flirting With Your Boss Won’t Be Easy:

Workplace relationships, especially the ones between supervisor and employee, are prohibited.

So beware of the possible consequences of getting into a relationship. A workplace relation can put both of your jobs at risk.

How To Flirt With Your Boss
Flirting With Your Boss Won’t Be Easy

If your boss isn’t welcoming this behaviour, you might get charged with sexual harassment. And harassment will get your job terminated immediately.

You’ll ruin your reputation and trustworthiness at work. If that’s so, it won’t be worth it to flirt, right?

4. How To Flirt With Boss – Take Societal Norms Into Account:

If your flirting doesn’t harm your reputation at work, it can still make you notorious in society.

Other coworkers will look down on you. They might even get jealous when you are getting special treatment because you flirt.

So consider the consequences to avoid any social embarrassment. In some worse cases, your relationship with the boss might end up badly.

5. Be Very Careful To Move Forward:

Suppose you have decided that it’s worth the risk and you want to flirt with your boss. Then be careful with your every step.

Be Cautious As Flirting Is A Dangerous Game
Be Very Careful To Move Forward

As there is a long line of possible risks, you need to adopt a sensitive approach.

You should learn how to deny that you were flirting if someone catches you flirting. So flirt without looking like you are flirting.

6. Look Into Her Charming Eyes:

The only tool you have to convey your likeliness to someone is your eyes. And flirting begins with consistent eye contact.

Eye Contact Is The Most Effective Tool In Flirting
Look Into Her Charming Eyes

Try to catch your boss’s eye during a meeting and hold on to that gaze for more than usual. Look directly into your boss’s eyes when he speaks to you.

Pay attention to how you’re getting interpreted because excessive eye contact can be creepy.

7. How To Flirt With Your Boss – A Smile Is The Key:

There’s nothing more appealing than a genuine, subtle smile when it comes to flirting.

Throw a real smile towards your boss, and don’t worry about the wrinkles you have.

It’s hard to learn to smile, but you think of something hilarious and then look at yourself in the mirror.

8. Catch A Close Sight Of Him:

Observe when your boss tries to act friendly to you. See the moments when he seems interested even if you weren’t excited about the matter.

Be Attentive To The Signs Your Boss Is Giving
Catch A Close Sight Of Him

You can flirt back by asking follow-up questions. Show your interest through your comments and gestures.

But remember not to overact. It’s more important to be genuine than to pay attention.

Mimicking his body language is a great way to show you are attentive towards him.

9. A High-Five Can Be Worth It To Flirt With Your Boss:

It’s a risky move while flirting with your boss, yet it’s most effective to show your interest.

But don’t move forward until you get positive feedback for the previous gestures.

How To Flirt With Your Boss
A High-Five Can Be Worth It To Flirt With Your Boss

An easy way to do this is to offer a handshake and smile at the end of a meeting.

When you’re speaking to your boss, give a gentle touch on his arm or forearm. But avoid any overtly affectionate or sexual touching in the workplace.

10. See How They React Back:

It’s a dangerous game to flirt with your boss. So you must pay close attention to the feedback you are getting. Slowly interpret that feedback to see what your next move should be.

See If Your Boss Response Back
See How They React Back

If your boss is reciprocating your eye contact, then things are going well.

However, if the boss is going out of his way to avoid you, then it’s time to quit your flirting immediately.

11. How To Flirt With Your Boss – Don’t Do Anything You’d Repent Over:

Romancing with someone out of work is easy. You can send them flirty texts or emails without any fear.

But you should avoid written communication in a workplace romance. Because if things go awkward, you can’t take these actions back.

Avoid Doing Anything That Can Cause Embarrassment
How To Flirt With Your Boss – Don’t Do Anything You’d Repent Over

Remember never to flirt in front of someone else or other coworkers.

Your boss can track the emails sent or received through a company computer. So you need to beware!

If your flirting gets reciprocated and your relationship proceeds, communicate by a personal computer.

12. Keep Things Straight and To The Point When You Are Flirting:

Either you or your boss will have to make a move if your relationship is proceeding. Workplace relationships are always complicated.

So you must stay honest and direct rather than getting considered as a sexual harasser.

Be Honest While You Flirt With Your Boss
Keep Things Straight and To The Point When You Are Flirting

Directly communicate your intentions to your boss and wait for his response. It might sound awkward, but it’s necessary to see if your boss thinks the same.

You can ask your boss for a coffee or lunch outside and talk about it there.

Pro-tip: It’s better to get less embarrassed that you misinterpreted things. Rather than the embarrassment after trying to kiss your boss.

Frequently Asked Questions

How Do You Flirt With Your Boss?

Flirting through eyes and smile is enough as it'd show your intentions to the other person. Try giving compliments to your boss. You can also try flirting with a gentle touch. But make sure it doesn't look like harassment.

Can A Boss Date Their Employee?

Although it's not illegal for a manager or boss to date his employee, the law controls sexual advances. Unwelcome flirting or sexual harassment can turn into severe consequences.

How Do You Date Your Boss?

Be sure of where to draw a line and beware of the possible consequences of a breakup. Think wisely and don't demonstrate too much. Maintain your performance in the office to keep a balance between work and romance.

Are Workplace Romances Unethical?

Workplace romance can result in increased favoritism. In some cases, it can also cause a hostile work environment and sexual harassment. So workplace romances can cause ethical issues both for employees and the company. It also impacts productivity.


People get attracted to their bosses because they hold a dominant position. It can be an attractive quality for most of the employees.

It’s human nature to get attracted to power and wealth. Bosses are already aware of this, which is why they get shy from people attracted to them.

But if your intentions are pure and you like your boss for his personal qualities, it can be different.

However, flirting with the boss needs careful steps, and you should know the art!

We’d love to read your experience in the comment section below.

Last Updated on 2 months by

Shahzaib Arshad
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