Category: Dating 101, Tips For Chicks | By:  Anna Jorgensen | 2 Comments


Flirting With Authority!

Question Sent in by Longing In The Tooth For You

I got an inquiry about how to let a man in an authority position know you’re interested, so if you want to know how to flirt with your boss or any man “above” you *wink* read on!

(If you’re the super supervisor, this advice does not apply, Girl Boss. Sorry.)

Here’s her tale … (summarized and shared with permission):

Long story short, she found her dentist attractive and felt chemistry growing after a few appointments. After one appointment, he personally called her to check up on her.

One time, she was at the front desk while he was standing at a distance staring blankly at her. She stared back a bit longer than she normally would.

She mentioned a tummy ache (on another occasion), and he asked if there was anything he could do.

Her question is: how can she convey that she’s single? Should she mention a bad date the night before?

How To Flirt With Your Boss / Dentist, etc…

  1. Ask yourself: If I do get into a relationship with this person and it doesn’t work out, will I have to find another job / dentist / doctor? Is it worth the risk?
  2. If the answer to #1 is “yes,” then know that you’ll have to be a bit bolder with flirting because men—and women for that matter—in authority positions may be (or feel) restricted from asking employees / subordinates / patients out due to professional ethics or HR protocol.
  3. Be bolder: ask personal questions. This is a great way of breaking through the professional barrier. Example: “I noticed you don’t wear a [wedding] ring. Too busy for love?” Hint: A man you’re flirting with doesn’t mind cheesiness! If he’s been giving you signals of interest (and if your natural personality is bold), you can add a cheeky grin and/or “sparkly, mischievous eyes” to the statement. Remember—men don’t speak hint. Be bold!
  4. Don’t talk about other men. The fellow of your affection will focus on the fact you were with another guy, not the part that states you’re single. Instead …
  5. Do talk about how you think you “might be ready to get un-single … if the right guy comes along” and if you’re really bold—or he’s def definitely showing signs of interest—you could add, “with a good eye for dental hygiene.” *cheeky grin, sparkly eyes* If he takes the bait, then ask about a restaurant nearby that you’d like to try: “Have you ever been to X? I’ve been meaning to try it.” Unless his answer is that X sucks, you could say, “We should go sometime.” Again, this is only if he’s been clear about his interest. (More on that shortly.
  6. If he doesn’t take the bait or he hasn’t been clear in his interest, you could say, “This might be kind of bold, but you’re very handsome. Do you get hit on by employees / patients?” You’re complimenting him and letting him know you find him attractive in a subtle way while broaching the professional protocol subject. Explore the topic based on his reaction.
  7. And finally, don’t just stare—instead, stare and smile invitingly!

Basic Signals that A Man is Interested in You

  1. Dental Dreamy stares at you. (Unless, he’s mentally distracted and simply not paying attention.)
  2. Hot Boss pays extra attention to you that he doesn’t give other women.
  3. Doc Dreamy asks questions about your personal life that have nothing to do with your health, particularly if the answers might reveal your relationship status.
  4. The Boss compliments you on your appearance, whether physically or fashion. (If he compliments you on shoes, there’s a 30% chance he’s gay. JK but not really JK.)
  5. The Doc’s smile brightens or his eyes sparkle in your presence. Yup, men sparkle, too. 😉

Men love when we flirted with them!

Men’s greatest need is sexual validation. This doesn’t mean being overtly sexual—nope! It means letting a man know that his physical presence is attractive—yes yes yes!

AJ RX: Get out there and flirt, ladies!

xo
Anna

p.s. Fast track to getting any guy you want here.


About the Author Anna Jorgensen

Dating, Love and Relationship Coach Founder: Wingmam, Vancouver, Canada Warning: Not PC, not a feminist ❤️


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  1. Do you have any idea what kind of chaos these relationships cause in the office for those of us who just want to do our job and not fuck the boss? Ugh. This kind of immature behavior should never be encouraged in a professional office.

    1. Answering a viewers question. If you don’t need the advice, don’t use it. Thanks for caring enough to share your thoughts, D.

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