How Can I Find Out If My Manager Is Attracted To Me?

A question to Ask the Workplace Doctors about flirty talk between a manager and a much younger employee.  How can the employee find out if the manager is really interested?


Question: I’ve only worked with my manager for a little over a year, but the past couple of months he’s been really flirty with me. (I work in a restaurant.) Let me start off by saying its not bothersome to me whatsoever I just kind of want to get an outside opinion to see if it’s just me or if there really is something weird. First off, he is flirty in general with a good amount of people we work with, however sometimes I think he is more flirtatious with me than anyone else.

This all started in March 2016, he got moved to manage a different store. At the time I was crazy upset because I had worked with him for a long time and I truly liked him as a person so on my days off I would go and visit him at his new store and we’d chat for a while. Nothing major. Then one night I was closing at my store and he sent me a text saying hey. I responded just basic stuff asking him how his new store was and it was all work related and then he brought up his vacation. He sent me pictures from his vacation he’d just gotten home from, which I guess is fine, and then he brought up how much he missed me. This was around 11:30pm-12:00am ish. So a little weird but not too odd.

The next day I texted a girl I work with that is 18 and really pretty that any man with eyes would be into and asked if he had texted her too and she said no she hadn’t heard from him. Then the next night, he came to visit me at my store while I was closing and said to me, “I hope your mom didn’t find it weird I was texting you so late at night.” (I still live with her, I’m 17) I responded with “no she honestly doesn’t care” and he said “okay good, I was watching you on camera last night while you were texting me at work” and at that point I was a little too stunned to say anything so I just laughed it off. He was not supposed to have access to those cameras since that was no longer his store.

A couple weeks later, he approached me about becoming a trainer for the restaurant. I thought it would be fun, since I’m friends with a lot of the current trainers so I said “yes but how old do you have to be?” (All the current trainers were 18 at the time) then he said, “well I think it’s 16, how old are you again?” And I told him. He responded with a big smile and laughter as he said, “old enough for me..” Kind of strange and I didn’t think much of it until a coworker that happened to be walking by, heard what he said and said, “what did you just say to her?” And my boss responded with “well I said she’s old enough to be a trainer” the coworker suspiciously nodded his head and moved on.

Maybe a week after that, my boss was transferred back to my store. The day he got back was Saturday, which he spent most of in the office doing paperwork for his return and for several other things. At the end of the day, he came up to me and said, “I’m really sorry (my name). I really hope you’re not mad at me.” “For what?” “Well because I spent the whole day in my office, I didn’t get to see you at all. I missed you today.” Keep in mind, his office is in the back of the restaurant not even 20 feet from where I work. “Oh it’s fine I said, I’m not mad.” That was very strange, and then the next time I saw him, he told me how cute I look in my uniform. We all wear the same uniform of a T shirt tucked into jeans and a baseball cap. Then he told me my eyes looked really pretty in the sun. On a different shift, he was mad at someone and I was doing my job, stocking things and he came up behind me telling me about his stress and said, “I wanted to come talk to you because you always put a smile on my face and make my heart feel warm.” I said “aww I’m sorry you’re having a rough day.”

I’m just not sure. I know I sound like an idiot because reading it now it seems so obvious that he’s into me, but he’s a pretty flirty person. I’m just not sure if he’s into me. I kind of want to make a move (as I really don’t have an important job, I’m an hourly employee at a fast food restaurant, and in the area I’m in it’s not hard for a teen to find a job) 17 years old is legal in Texas, and I’m not looking for a relationship because of the age gap (he’s late 30s) maybe just a hook up. So I guess my question is, do you think he’s into me enough that I could make a move and not make him feel awkward?

Response: Thank you for sharing your workplace issue with us. It certainly sounds like your boss is very attracted to you—to the point of making sure you know it. I agree with your first thoughts that watching you on camera and texting you while you’re nearby, are both a bit weird for someone his age and in his position. It’s one thing for him to be attracted to you and another for him to be tracking you in that way.

So, my first advice is to be cautious about how you interact with your manager, even if he seems completely trustworthy and harmless. The reason so many older men get involved online with teenagers is because the age appeals to them—not the girl, just the age. If his mind works like that, his other actions–especially if he were to feel rejected–would not be good either.

However,  let’s assume he is nothing more harmful than a late-30’s manager who thinks you’re cute and nice to have around and he enjoys the laughing conversations and the support you give him.  That still doesn’t mean he is willing to jeopardize his career to have a few sexual encounters with you. Even if he is willing to take the chance, you don’t want to be part of something with consequences that serious.

To you, this is a temporary job. To him, it’s his sole support now and the foundation for his future. You know very well he would be fired, if it was found out he had gotten together with you outside of work. He would probably be sanctioned for what he has already done and said. (And, if one employee overheard something and reacted to it, you can bet other employees know about it too.) Even if you quit so the two of you could get together, he could be sanctioned severely for the appearance of impropriety, if someone found out he was involved with a former employee–especially one your age.

Here are the other problems with getting together with him, for just a few casual sexual times:

1. You are still a very young woman—still an adolescent in most things—and are developing your self-image and your decision-making abilities and interpersonal and communication skills. Going from flirty talk to having sex without having a more established relationship may be part of your life now but making it a habit as you go from job to job is not the person you want to become. Every time you do it, it will be easier the next time and ultimately that will become what you do all the time. There is no career or life development involved with that—just sexual experiences. If you have never had a sexual involvement with a boss or coworker, there is no point in starting now. If you have had such an involvement, count yourself lucky that nothing bad happened as a result.

I’ll be very blunt about it, you could probably find a way to get with him for a quick session with either or both of you using your mouth or your hands for some sex play or you could cram into the back seat of a car, try to fit together and come and go in a few minutes. It would probably be somewhat exhilarating at the time, but it wouldn’t be really fun because it would have to be hurried and sneaky. It wouldn’t present you looking your best or showing that you are mature–and it wouldn’t be respectful of either of you. If you go someplace more private so you could have a bed for your activities, you increase the risk of being seen and you catapult a fun flirtation into something much more difficult to get out of later on.

2. Your work will become very uncomfortable if it turns out he’s not so attractive when you take away the manager-employee aspect. How can you keep flirting with someone who starts to turns you off rather than on? There goes the fun!

3. He may want more of a relationship than you do. There is nothing worse than dealing with that throughout a work shift. And, if he already tends to keep an eye on you, it might be even worse if he became jealous or needy.

You mentioned that you probably could find other work if you had to quit this job in order to get together with your boss. If you wanted a real relationship, it might be worth it to do that, to allow the two of you the freedom to get together and see what happens. But, it doesn’t seem worth it to do that for what might end up being only one time together. Given your age difference, it probably would not be more than a few times, at most. And, if your boss really does enjoy having you around and you enjoy working with him, you’ll have ruined those times together.

The bottom line: My advice is to enjoy appropriate interactions, but tone them down for the sake of both of you. Don’t make it obvious to other employees or other managers that there is a special bond between the two of you. Besides, spending a whole shift essentially teasing each other is very frustrating and distracting.

You have work to do and your boss certainly does. You can help him be successful by being a sparkling and energetic employee who he can fantasize about and occasionally talk to in a more personal way, but who won’t cause him any harm. He can help you have fun at work without harming you either, by having a warm feeling about you but not acting on those feelings. Help him and help yourself in that way.

Here are some general guidelines for keeping you and him out of trouble:

1. Don’t be alone with him unless there is a way to have a door open.
2. Don’t talk about him to others in any way except to discuss boss-employee issues.
3. Don’t have conversations where you have to lower your voice so no one else can hear or where you use coded language or non-verbal communication to convey something more personal than you can say aloud.
4. Discuss work more–and personal things less. Keep his focus on how well the establishment is going and how good that is for all of you.
5. Plan your future and use your current job as a learning experience to help you achieve all you want to achieve five, ten, fifteen or twenty years from now.
6. Keep yourself, your life and your character safe.

I realize that all of this goes past answering your basic question, which was to inquire if there was a way to let your boss know you’re available and attracted to him, without making things awkward. The easiest way to do that is to say something when he’s made a complimentary or flirty remark: “Very sweet and cute of you, Kevin! I’ll bet we’d have fun if we could get together away from here, but I guess somebody might think that would be a problem, right?”

That will almost inevitably start a conversation then or later. If he doesn’t intend for his flirting to go further than work, he’ll back-pedal right away. If he’d like to give it a try, he’ll let you know. Then, you can get out of it by saying you don’t want you or him to lose your jobs over it. If he pushes it, a surefire way to stop him would be to tell him you’ve asked your mother about it and she advised you to just be friendly at work, but nothing more than that. (“The words, “I’ve talked to my mother about it….” works like a bucket of cold water!)

Best wishes to you with this situation. If you have the time and wish to do so, let us know how it works out for you.

Tina Rowe
Ask the Workplace Doctors


Tina Lewis Rowe

Tina had a thirty-three year career in law enforcement, serving with the Denver Police Department from 1969-1994 and was the Presidential United States Marshal for Colorado from 1994-2002. She provides training to law enforcement organizations and private sector groups and does conference presentations related to leadership, workplace communications and customized topics. Her style is inspirational with humor.