How to Tell if Your Boss Likes You in a Romantic Way

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Is your boss bringing coffee or doughnuts to your desk, or giving you little gifts when no one else in your office is getting the same attention? If so, your boss probably has a crush on you. At one time or another, most people need to deal with a co-worker flirting with them.

Bosses flirt with employees, too. Interoffice romances used to be more common, but there are now more workplace rules about such behavior in most companies. When people work together 40 hours a week or more, there’s bound to be flirting.

Even though having a relationship or dating your boss is taboo in many workplaces, it does work out positively for some people. You may be confused about how to tell if your boss likes you in a romantic way because supervisors may send out mixed signals when talking to you.


You may assume, at first, that your boss is just trying to be friendly or reward you for being a good worker. However, if the behavior continues and there’s no viable work-related reason for it, he’s flirting with you.

A supervisor flirting with an employee is frowned upon in 21st Century culture. For most of the 20th Century, if a boss flirted with a female employee, some women took it as a sign that she could move up in the company (or marry her rich boss).

Some women even purposely flirted with their bosses as a means to get married or promoted. (Think of some of the scenes AMC drama “Mad Men,” set in the 1960s.)


Sometimes the flirtation is so subtle that you may be confused. You don’t want to seem paranoid or suspicious by calling him out on it if the behavior is unwanted. You have to decide whether the flirting is welcome or not, and how to deal with it.

Signs Your Supervisor is Romantically Interested in You

Sometimes it’s hard to determine how to tell if your boss likes you in a romantic way. Friendly people talk to everyone in the workplace and may even hug people or shake hands often in a non-flirtatious way.

You don’t want to act like you see flirtations in innocent actions, so it’s important to look at the context and situation as well as words/behavior. The frequency with which a boss says or does different things is important to note as well.

Gifts

Any gift your boss leaves for you that’s not work-related is inappropriate. Gift cards to Starbucks or a casual restaurant or branded company merchandise are common gifts for employees celebrating a birthday or work milestones. Flowers, jewelry, or expensive gifts, however, should only be exchanged away from work (if you’re okay with a possible relationship).


A personal or expensive gift that your boss doesn’t give to other employees can be considered special treatment.

Texts, Calls, and Emails

Receiving texts that have little to do with work, or texts about matters that have long been dealt with indicates that your boss likes you in a romantic way. Anyone can make a mistake and send a text about a long-solved matter once in a while, but if it happens frequently, and at odd hours, your boss is probably interested in you in a romantic sense.

He Adds You on His Social Media Accounts

Companies commonly look at your social media before they hire you. After you’ve been hired, some companies may want you to avoid adding co-workers or bosses to your Facebook or Instagram, while other companies have no rules about social media use.

It’s one thing when a work friend adds you to their social l media if you know each other well and have a rapport. Your boss shouldn’t add you to his social media unless he generally adds employees and other supervisors to his friends/followers list.


Your boss may be adding you to his Facebook or Instagram to find out more about you, particularly your relationship status if you haven’t been forthcoming with the information during flirtation attempts at work.

He Changes the Subject During Meetings

Your boss may veer from the subject matter during one-on-one meetings, or schedule a business meeting that turns out to be about personal subjects. Your boss is flirting with you if he comments on your physical appearance, asks about your dating status, or mentions his dating history.

Physical Contact

Any supervisor who would touch you by rubbing your shoulders, etc., especially in public in front of other employees, shows poor judgment and wouldn’t be a good prospect for a boss-employee relationship.

Bosses who are more subtle with their physical contact (they may touch your shoulder when you’re upset about a work mistake, or hug you after a promotion) may be flirting with you or be a kind person.

He Makes You Transfer Departments with Him

A manager may transfer you to a new department every time he gets a new position within the company. He may do this because he appreciates your work ethic and knowledge and believes you’ll be an asset to the department.


He may be interested in you romantically if you aren’t really suited for the tasks in the new department, or if other people were first in line for the position and you got it instead.

Your Instincts Tell You He’s Flirting

Trust your emotions and gut instincts when you’re around him. He’s probably flirting if your instincts tell you he is, especially if your gut tells you he is over several days or weeks.

You can ask him work-based or neutral questions to gauge his moods and see if the flirting is sincere, or if he has an ulterior motive besides a normal dating relationship.

He is Too Helpful

A boss who always helps you on work projects, or makes suggestions, may be using it as an excuse to spend more time with you and flirt with you. Sometimes, a supervisor helps you because he sees that you have potential and wants to see you succeed.

Determine if your boss is being too helpful because he has a romantic interest in you be observing how he interacts with other employees. He may just be a good boss if he’s helpful with everyone.


He may be flirting with you if he exhibits other flirting behaviors (gifts, physical contact), and doesn’t offer other employees the same assistance.

He Exhibits Flirtatious Body Language

Your boss might walk up to your desk unexpectedly, lean over and start talking to you, or he may touch your shoulder. In a business environment, people will get your attention by speaking to you in a neutral tone of voice, emailing or calling you on the phone for a meeting, or use other professional means to get your attention.

Check to see how your boss acts with other employees. He may be overly friendly or invade other people’s personal space, too. If not, he’s probably singling you out for flirtation.

He Schedules One-On-One Meetings

Having private meetings with your boss about a project you’re working on isn’t flirting – unless your boss asks your personal questions during the meeting, or exhibits other flirtatious behavior.

Any private meeting that takes place after work, or is not about a relevant work project should be considered flirtation.

He Confides in You


Your boss may relate personal details about his life to you that he doesn’t share with anyone else. A supervisor (or another employee) may do this because they trust you and value your opinion on the matter. Sharing secrets, however, is a way to strengthen a relationship or friendship, or figure out if you’re worthy of more than flirtation.

He Gives You Work Benefits

Perks such as major work assignments, flexible hours, or extra vacation time are usually a result of seniority or an excellent work record.  You may receive perks more than others if your boss has a romantic interest in you.

If the perks you receive are inconsistent with your work record or seniority, or if other people never seem to get the same benefits, your boss may be flirting with you.

He Changes His Physical Appearance

A supervisor suddenly dresses up, has a different hairstyle, or wears a high-end cologne daily at work may not merely be prepping for a meeting with his supervisors or a job interview.

He may be trying to impress someone he’s interested in romantically. You may be that person if he exhibits several of the other behaviors on this list concurrently with his new appearance.

He Jokes Around with You, But Not Others


A sense of humor builds camaraderie and releases tension in the workplace. Some bosses joke around with their employees to help let off steam and brainstorm ideas. A boss who is happy and jokes around with you, but is serious around others may have a romantic interest in you.

Humor has various forms, though. Friendly jokes about work or something in the news is fine, jokes about sex and physical appearance go beyond flirting and may be construed as harassment.

He Makes Promises about Your Work Future

Your boss may be flirting with you if he exaggerates your work prospects with the company unless you have a manager who is encouraging and upbeat with all his employees.

Ask yourself if there’s a legitimate reason for him to compliment your work and promise you a better position with the company. He probably has a romantic interest in you if you can’t find any other reason for the promises.

He Asks You Out After Work

Your boss may ask you out after work for drinks. He may not exactly ask you out on a date, but he won’t mention anything about work-related matters, either. A friendly boss may occasionally have after-dinner drinks with employees, alone or in a group.


However, if your boss normally isn’t friendly with his employees, he may be flirting with you by inviting you out after work.

He Takes Your Friendliness for Flirtation

Your boss may develop a crush and you and become romantically interested if he mistakes your friendliness or optimism for flirting. You’ll need to let your boss know you were just being friendly if he continues to mistake your effusiveness for flirting.

The longer you go without saying something, the more likely it is he’ll say you were “leading him on” if you’re not interested.

He Laughs Too Loud at Your Jokes or Stories

When your boss laughs too effusively at your jokes, he either has a crush on you or is trying hard to flatter you. When someone laughs at your jokes to heartily, it may get embarrassing if you’re around a group of other people. This embarrassment may be amplified if the person in question is your boss.

However, if you have a crush on your boss ( or like him), you may find the situation endearing.

Unwanted Flirtation from a Boss

You need to put an end to unwanted flirtation, as it can severely impact your job, career, and emotional health if you continue to put up with it.

You have a right to complain to your boss and his supervisors if you’re experiencing unwanted advances.

There’s a difference between friendly discussions about work, or even neutral, after-work activities, and flirting. An outgoing or friendly boss acts the same around all his employees. A boss that singles you out for friendly chatter while remaining business-like with other employees may not only make you feel uncomfortable but will also make other employees resent you.

Let your boss know you’re seeing someone, you don’t get romantically involved with people at work, or that you’re not interested in dating anyone right now if the flirting seems innocent enough, but it’s still unwanted.

Tell the boss, in a calm way, that you want to focus on work, or you have a lot of work to finish if he touches your shoulder or compliments your dress or looks. His response will let you know if you should pursue a complaint with human resources.


Remember, the decision to follow through with the flirting is entirely up to you. Don’t feel powerless if the flirting makes you uncomfortable – you have options. You can compliant to your human resources department, your supervisor’s boss, or contact a lawyer if the flirting turns into harassment.

Whether you approve or disapprove of your supervisor’s romantic interest, it’s important to address it right away. Contact your human resources department or another supervisor first if you find your boss’s romantic interest overbearing.

Proceed with caution, however, if you do decide to pursue a romantic relationship with your boss. Be aware that a breakup may be messy and get you (and/or your boss) fired if the situation isn’t handled discreetly.

The Difference Between Flirting and Sexual Harassment

There’s a difference between flirting and sexual harassment. A flirtatious boss may bring you a Danish from the pastry cart, while sexual harassment involves threatening behavior (demanding you sleep with him or see him after work, or get fired or demoted.)

Even subtle flirting can become harassment if it’s unwanted. You need to let your boss know you’re uncomfortable with the flirting and want it to stop. If the flirting continues or becomes harassment, report the issue to people with the authority to deal with it.

Contact a supervisor who doesn’t work directly with the boss if there’s no formal procedure for reporting unwanted advances. You can also contact a lawyer or the Equal Employment Opportunity Commission (EEOC) if the flirting becomes harassment or if you’re demoted or fired due to rebuffing advances.

You don’t need to be afraid of losing your job if your boss retaliates against you for

rebuffing his advances. You have many resources to protect yourself and your job.

How to Respond if You Approve of Your Boss’s Romantic Interest

Check your company’s guidebook regarding office romances. The rules for conduct for employees and supervisors will be clearly stated. Companies also have classes and seminars regarding sexual harassment and inappropriate behavior.

Some companies strictly forbid dating co-workers or supervisors, while others permit it as long as the parties are discrete. Small companies may have no official policy on office romance.

Use your best judgment on how to proceed. Talk with him in private (preferably out of the office (lunch, break, waiting for the train, etc.) and let him know you’ve noticed his flirtations. His demeanor will tell you everything you need to know.

If the discussion is easy-going and friendly, you should have no problems navigating the romance; but if he seems demanding, tell him you feel uncomfortable about the situation. Trust your instincts about his personality.

When You Decide to Date Your Boss

Once you decide that you want to date your boss, you need to discuss how to conduct the relationship. Do you want to keep it a secret, or let others in the office know you’re dating? Even if you genuinely like your boss as a potential love interest,

Your co-workers may catch on to the romance even if you decide to keep it a secret. Be prepared to deal with the possible fallout (jealousy, jokes, being ostracized from other work friendships) if you do decide to date your boss. Every workplace is different.

Your company’s upper management may not respond favorably to a boss dating an employee, even if it’s not expressly forbidden. Your career is more important than a fling with your boss. You should think twice about a relationship with your supervisor if upper management disapproves of it.


Be aware of and accept the possible consequences if you do decide to date your boss. It’s best to stay discreet and disclose as little about the relationship as possible to people in your company or industry. Rumors can get started easily if you talk too much.

Maintain your distance and professionalism in the office. A couple that can’t concentrate solely on business in the office should reevaluate their behavior. It might be a good idea to transfer to another department (or even get another job, if you can) in order to maintain the relationship and your professional reputation.

Every situation is different. There are plenty of examples of boss/employee romances or co-worker romances that succeed. The key seems to be the seriousness or bond between the people before they commit to dating or romance.

What About a Female Boss Flirting with a Male Employee?

A female boss demonstrates the same basic flirting techniques when flirting with a male employee as a male boss does when flirting with a female employee. Be attentive, and make sure she’s not demonstrating behavior that’s merely friendly or helpful.

Follow the same steps as a female employee would if the flirting is unwanted. Be careful if you decide to pursue a romantic relationship with your boss. Consider the consequences if the relationship ends – you could lose your job, and it may ruin your reputation in your field.

How to tell if your boss likes you in a romantic way involves the same signals regardless of your age, sex, industry, or your supervisor’s age or sex. Older male bosses may be more “handsy” or crude than young men, due to the attitudes and morals they experienced when they were younger.

Young male bosses are more familiar with modern workplace etiquette, so they’ll normally be more subtle if they do flirt with you.

Conclusion

Office romances aren’t as popular as they once were, but they’ll never disappear completely. Many people spend more waking hours with their co-workers and supervisors than they do with their partners during some workweeks.

Due to the sheer amount of time you spend with your boss at the office and at work functions or parties, you’ll naturally forge some sort of relationship, even if it’s strictly business or friendly.

It stands to reason that some bosses will become attracted to employees and vice-versa. Office romances only turn out well if both parties are equally interested in having a relationship.

Learn to recognize the signs that your supervisor has a romantic interest in you. The sooner you verify his intentions, the sooner you can get to know him better (if you want to date him) or politely decline his flirtatious advances if you’re not interested.

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