I'm a female boss having an affair with a male employee. I'm in a crazy difficult situation. What should I do?

[Anonymous]

I’m a female boss sleeping with a male employee who is a lot younger than me (I’m 41. He’s 23). It’s not an “affair” per say because both of us are single, but I still always feel like I have to keep us a secret because of the fact that I’m his boss. A huge part of me thinks I need to stop. He’s my employee and if we got caught we’d both get in huge trouble. Moreover, he’s way too young for me and I know it. I started this affair against my better judgement, but I largely did it because I developed real strong feelings for him). I’m a single woman who has been divorced twice with two kids who both go to college out of state (I had them both pretty young). My kids do call me regularly, but even so I often had felt lonely. Shortly after he started working for me we immediately connected. We had a ton in common and could talk endlessly. He could always make me laugh and he was very warm. I eventually started talking to him about personal issues/struggles I had. He was an excellent listener/I could tell really cared. I developed strong feelings for him. Combined with finding him very physically attractive, I started to go crazy. I latter found out he felt very similarly. We eventually broke down and slept together. The next day I told him and myself it was a huge mistake, we can never do that again, “…but it was really good.” To make a long story short we’ve been sleeping together regularly every since.
We’ve tried to stop a couple times, but it never lasts long because we always both get sad and want something more than a strictly business relationship. He’s thought about getting another job, but this job is a huge opportunity for him and I don’t want him to pass it up (and I'd miss him). Moreover, I know he’s way too young for me, but I still have stronger feelings for him than guys I’ve been with who are my age.
I’m really confused and I’m going crazy trying to figure out the best thing to do is. What should I do with him/the relationship/our jobs?

[EABsTUQ]

Why can't you date him? Is it against the company policy? Enough about age. You're not manipulating him or something, he is a grown man. If you wanna be together then find a way. There is a way but first you have to make the decision of whether or not you want to date him. You clearly haven't even made the decision but yet you're worrying? You want to date him yes? Okay make the decision that you are going to date him. Next you need define what you want it to look like. If there is an issue then find the solution to the issue. The answer is there if you go looking for it. It always is. If you two just wanna have sex then I doubt anyone will ever find out as long as you do it in private places. But please for your own sake do not shame yourself for liking a young man. There is part of you that you are shaming. Love yourself and understand that it is perfectly okay to have feelings for him and also date him. You're 41 live your life before it's gone. You didn't come here to play small ball.

[cntrytbm]

It is definitely tough to date someone you work with. It's even tougher if you are the boss. Let's say you're in quite a situation. And the age doesn't bother me but I think you have to break it off mutually if you're going to keep your job. If you break it off in such a way that it hurts him or pisses him off then he may use that as leverage against you. Since he is younger he may not be mature enough to handle the rejection maturely. I get where this can happen though. You spend so much time at work, and a lot of cases you spend as much or more time at work than you do at home and at home you're sleeping a good portion of the time. So the opportunity to build a solid relationship is stronger at work than sometimes with your own spouse! I know you said you are not married, but the analogy still fits I believe. I do think you need to break it off but be careful. I'd hate to see you lose your job and your boyfriend.

[Anonymous]

I don’t know tbh. It’s your life and your choice. So what if you’re his boss? Lots of people marry people they work with. If you’re both happy then start a relationship or whatever who gives a shit I mean life’s too short.

Personally I think that age gap is quite big and I wouldn’t do it myself because I’d feel like he’s a kid and young enough to be my son. I mean I’m 22 and my mum is 43 so it’s similar age gap between you and that boy but I guess if men can marry girls 20 years younger than them and they don’t care then what’s the problem if you do what makes you happy? Nobody bats an eyelid when 50-year-old men romance 25-year-old girls in movies who are young enough to be their daughters.

[Smoke-n-Growls]

You mentioned the job he has is a great move for him.

Is it time to consider a diagonal move for you? If you're nearing the end of your progression in your existing company, and you really love this guy (which it sounds like you do - you don't seem to be someone too eager to endanger her career), what if you moved?

Either way, you two can't continue being boss-employee and you both can't seem to not be sleeping together.

I'd be careful - you have a lot more to lose in this situation. He's likely to keep his job and station, you're not.

[Desconhecida]

You should stop the relationship right away

[yucychan]

Wow, what a predicament you've have got yourself stuck in.
I get the "you feel lonely and you need someone to love you", I totally do. But what you are doing is so ethically and morally unacceptable. It's not the age difference. It's the fact that he is your employee and he is reporting to you. I think you are more than well aware of your own company policies regarding personal relationships in the office. And how it constitutes a very bad case of conflict of interest.
Have you considered the consequences and repercussions if either one of you were caught? That both of you might lose your jobs?
My advice is either one of you leave your current job or end this relationship altogether.
However, seeing how you two are into each other, ending the relationship may not be possible. Either one of you have to be transferred out.

[modelUN242]

You're being unprofessional as a boss doing that. What if it was a male boss doing it with a female employee, it's still unprofessional, and a conflict of interest. No dating in the workplace especially your superiors. Break up with him, he's much younger (mom and son kink) than you and only see you as his fun toy. He will dump you and you will feel terrible because younger guys see older women in that way. "He’s my employee and if we got caught we’d both get in huge trouble." If common sense kicked in, you would have stopped it. I understand that you're lonely, but there are plenty of single men your age and would love a committed relationship. This guy will break your heart, c'mon, think about how your college kids would feel if they found out that you were sleeping with a guy their age!! Overall, it's not worth your reputation, his, your job, his job, and your dignity. You're a grown woman, let him go and encourage him to do that other job.

[SuccessfulHornDog]

Actually it is too late. If she breaks up with him and he gets mad all he has to do is claim victimhood #metoo. She can't protect herself from that. Even if it was mutual the precedent has been set. she is in a position of authority over him and that makes it wrong. She would lose her job and face public embarassment

[modelUN242]

@SuccessfulHornDog Lol good luck getting a metoo moment as a guy, it was created by women for a reason. We as a society still have a bias with women being the victims, so I doubt that. I know some cases where there was a metoo filed against a woman, there was a female doctor who was having a sexual relationship with her cancer patient but I think he made complaints after she broke it off, so maybe.

[SuccessfulHornDog]

So you acknowledge that it is a double standard. should women who do the same thing lose their jobs and be publicly ostracized? Here is the problem if you don't... The whole #metoo thing will lose its power because people will recognize that it is not really about people in a position of power having a sexual relationship with an employee.

[modelUN242]

@SuccessfulHornDog Yeah, I guess, but if a woman takes on a masculine position like boss, there should be consequences. And there shouldn’t even be a metoo in this case! Anyone who files a metoo in this time of case are douchebags, so depends on the guy I guess. I mean the metoo has lost credibility but it has done some good, I think co-ed work environments are problematic.

[SuccessfulHornDog]

co-ed work environment are good. We compliment each other. Women are better at some things and guys are better at some other things. I dont think its a problem but I object to thinking that double standards will solve inequality.

[JPrez]

He's young and inexperienced. He doesn't know any better and sure he can have sex but he is probably not emotionally mature. He may be confusing the sex with love and he just knows he's getting laid regularly. He may not know that there is not much of a future with you (sorry - just being honest) but eventually he'll figure it out. I'm 50 too, so I can relate. You should never get your money and your honey in the same place. When you get a chance, you need to end it, and one of you needs to get another job. Good luck...

[Finchie40]

The age thing isn’t really the issue , the having sex with an employee is , Mainly because your job might be at risk now and the fact that he can easily blackmail you and take advantage of you. So you pretty much already dug the grave so you my as well keep screwing him and keeping it a secret as much as possible and ride it out and see what happens , but most important thing is if he doesn’t want to have sex with you anymore just stay friends with him and let him go considering I highly doubt this 23 year old is going to move in with you and get married to you , he will eventually find someone else , sorry to say it that way and be blunt but I don’t see him settling down at his age , so hate to say it just look at him as a fuck boy a FWB’s Control your feelings toward him , just use him for sex but don’t let it turn into love

[BeenThereLovedIt]

Age is meaningless, with one exception- Your life story is already written and your are established. His is not. What does he want out of life? Kids? Family? Homestead?

There's nothing wrong with being with him if that is what you both want. Age means nothing when applying love to the equation, and if you both want love, then go for it, but you need to make sure he understands what he will be giving up - his youth and part of his future, to be with you.

I'll spare you a lecture on sleeping with subordinates, I'm sure you are aware that it's not ethical and could get you both fired, but at the same time it's also not illegal. Understand the risks you both face currently and moving forward.

[broken_heart_at_48]

Why is the age thing such a big deal to you? Are you worried about what others will think? The only ones I'd worry about are your kids. I'm guessing they're roughly the same age as your guy. That can be a huge problem but it depends on how open minded your kids are. For me if my kids were going to have a problem with it I would end it or at least keep as a friend's with benefits type thing with the understanding that no one can know. Odds are it's gonna get out so I'd be back to ending it. Now the job issue is a no brainier. If this is something that can get both of you fired you have to end it. So it should be simple but going back to being lonely is a hard choice to make but is it worth causing problems with your kids and being fired for a relationship that more than likely won't last anyways

[Bang5luts]

I think it might be a good idea to look into getting him or yourself transferred into a different department, or maybe somehow finding a way to make sure hee could keep his job and not have to be your subordinate. Because it will cause problems down the road. But after two marriages not working out, it might be time to take care if your needs a little. Also, check with HR or in your company's policy on intercompany relationships. But without letting on to anyone about your relationship with the guy your seeing. Good luck! I truly hope it works out..

[Tunasub]

Is it possible for him to go to another department? That is tough I must say I know by experience. I was sleeping with someone I supervised. It made for an awkward night if things went shitty during the day. I started to have her train in another department. Lateral move so nothing changed and eventually I was no longer her boss but we still worked at the same place. Eventually we split but probably would have been sooner if she didn't transfer. Maybe that could help your situation. Good luck... oh Huggies are on sale this week...😂😂🤣 Kidding lady... got to keep it light... get your groove back Stella.. I ain't mad at ya...😉

[Crimsonstorm]

I think you worry too much instead of just be happy. I know it is just natural for rational mind to come and poison your happiness but I will repeat it, you worry too much. Maybe just let things follow their natural course? If you two are so happy togheter I do not think any of you should give up that, just be happy. And I doubt about his age really being a problem... if he understands you you should be happy, if he likes you so much even better and no it is not selfish I am sure he is pretty aware of what he does... also women as they get older their beauty gets a lot more complex and intense and probably him not being superficial gives the opportunity to see your beauty as a whole and admire it and love you don't break it for him just be happy.

[pepperhicks]

"He’s my employee and if we got caught we’d both get in huge trouble." No, you as the boss will be the one in huge trouble. In an office environment, people pick up on an inter-office relationship very quickly. If any one of them can make a case that it negatively affected them at work, your job is gone. And if anything goes wrong with your relationship, he holds all the cards as to whether you keep your job. Does he really have such a great job at 23 that you want to risk your job over it?

[samiammm]

If you truly love him and want a relationship , it'll eventually koll your career.


If it's just crazy hot sex then it's not worth risking so much.


The Work relationship is messy
The age difference is too much

It's gonna be a difficult ride if you choose to continue.



Did you ever have a tlak with him?
Let us know his side as well and then decide something.

[SenseiSeptred]

Here is some advice for him and you, but since I am giving this piece of advice to you and you happen to reply back to this I expect no emotional garbage from you due to the code that I follow from another country in origin. Just both of you go on to a different job altogether as job equals with the same position even if it means a loss of major income for the both of you.

[jessicasissy]

First thing is first. You need to get in a position where you both won't lose your jobs. He needs to be in a different department or under another supervisor, there's no way this ends well if he's your direct subordinate and word of your relationship gets out at work. Once that's done you can figure out what you want to do with this guy with as little stress and pressure as possible

[_SOARER]

My advice is to tell him what you just told us
That you want him to be successful at your company. In order to do that you two need to keep your relationship completely out of the work place and avoid other co-workers as much as possible. Dont want them finding out.
You can keep it secret for maybe a year or 2 until he finds something better.

Work place romances happen there is nothing wrong.

You should talk to him about making a plan. Good luck ❤

[Unit1]

Ehm. Why don't you just let things be the way they are? It sounds to me like you're complicating it unnecessarily or introduce a self fulfilling problem where there is likely none. So what that you both like each other, slept together and are working in the same company? Nobody got hurt. If you don't want this to go around, don't you both talk about it. Simple as that. This is nothing new.

[djmzes]

Simple

[TheAfrikan]

If you truly love each other n it's not all about screwing each other like nuts. Then go aheadon a date and see how stuff works out. If you 2 connect well, and connects with your kids sell, your parents allow him. Then go ahead and be lovers.
We might be ready to see another couple like the one for the French president and her 65 years old wife 😎

[Freddy78361]

The relationship is fine. You aren't marrying him and he's legally an adult.
The job situation is not.

I suggest you fix the job situation somehow and soon otherwise both will get hurt.

[SomeGuyCalledTom]

It probably won't end well, but you're both consenting adults, so just remember what's potentially at stake (a young man's career prospects, your own reputation as a manager, etc.), and listen to your head and not just your heart.

[Thatsamazing]

1) Your ages don't matter, don't know why you'd even mention them, and 2) what is there do really do? If he leaves the job, then you have a chance anyway, if not, then as long as the two of you can really truly keep it under wraps, then why stop?

[NerdInDenial]

The age is not the issue. It's the whole positional authority. You put yourself in a spot to get blackmailed by anyone who knows this information. If you value your career, end the relationship immediately.

[DizzyDesii]

I see nothing wrong with it if you're both single and he respects you and your kids. And yea he prob should work elsewhere so that people dont think you're showing favoritism

[Avicenna]

The two of you will be in trouble even if it ends now, so I guess there isn't any real benefit to ending it. Just be careful and let things take their course.

[SuccessfulHornDog]

Are you ready for when it is over and he decides to report it? #metoo

[Asker]

It's a consensual sexual relationship. Believe me, he wants it just as much as me.

[SuccessfulHornDog]

I'm not saying otherwise but I think that what I learned from the #metoo movement is that because you have a position of power, you are in the wrong. Some (not me) compared it to rape because an older man held a position of power in the company and was having sex with a female employee. The person without the power can decide to go after you if things dont go their way. They can do this many years after it happens regardless of the actual nature of the relationship.

[Janenow]

He is not way too young for you. I know a 23 year old who is married and has a kid with a 50 year old and they are doing fine. Just be together with him. This is the best thing you can do right now.

[Asker]

When it comes to age I don't feel it a ton right now, but there are little things here and there that do come up that make me think it may come up latter. For example, he'll make references that someone his age would make and no one my age would even think of. He also has a fair bit more energy to go and party than I do. It's not that I can't go out and have a good time, but I do tire quicker. It's nothing huge, but it's a fair amount of little things that do add up enough to concern me a bit.
Then there's the concern of how my family will react when they find out I'm dating someone so much younger. I know that I'll have to go through a whole ordeal due to the age gap and that gives me a headache just thinking about it.
Furthermore, i am worried it could get to be a bigger deal latter as I age faster. Right now I'm in very good shape and do look fairly young for my age, but I'll still age faster than him. Finally, I know he does want to have at least 1 kid, but that may not actually end up being a problem. I'd be more than happy to have another kid (maybe even 2 if I can) if we get that far. However, I do worry that at my age I may have a hard time getting pregnant. I haven't seen a doctor about it though.

But even beyond the age concerns there's still the issue that we're both risking our jobs by doing this. He's told me he's looking for other jobs, but (in the current job market climate) he's having a very hard time and hasn't found anything. As of now risking our jobs is apart of the relationship, and that is a major concern to me. Part of me thinks I should back out, but whenever I seriously think about it I get really sad and don't want to. But then the only other alternative is to risk it, which is very stressful/scary.

[Archerer]

Sounds like a dream come true to me. What kind of work are you in? I would just keep it going as long as you won’t get in any trouble with the business.

[Asker]

It's not a dream come true. It's extremely stressful. I'm always worried about us losing our jobs. Sometimes I feel like we need to stop, but then we get really sad and start all over because we want to be together. Then there's the fact that he's way too young for me, but I still have feelings for him and want to be with him (even though I think it's so dumb that I feel this way about someone so much younger). A huge part of me also wants to stop all this mess and just go public, but we can't do that for a whole lot of reasons! However, I don't want to stop because I feel such strong feelings towards him and we make each other very happy. Even though I'm going crazy over this I've been happier with him than I have in a long time (which makes me even more stressed over everything!)
Believe me, it's not a dream come true. I wish everything was way simpler, but I'm trying to figure all this out

[Archerer]

Move jobs then

[AmeerX]

You can't buy just hands. You hire a whole human being. It is wrong to think such relationships are wrong. And if they are so wrong then stop hiring females in male workplace and males at female workplace

[humanearth]

Sounds like you fell in love with the young man

Why don't you find another job and married this young man

[michael1469]

Somehow document that he buys you gift or something as if it ever goes south that you unduly influenced him. But if you are happy and you know it bust a nut.

[mooky06]

He needs to get another job if you want it to be more then a business relationship. o

[SuccessfulHornDog]

He needs to? Why doesn't she get another job

[cntrytbm]

Because it makes sense for the older, career person with a more advanced partition to keep their position and the younger person in a lower level position to find a new gig.

[SuccessfulHornDog]

@cntrytbm The older person in this case is guilty of having power in a sexual relationship with an employee. Did you sleep through the whole #metoo movement?

[cntrytbm]

I don't GAF about #metoo and they're both consenting adults who still care about each other, so they should do what's logical, not what some F'd up group of society says they should.

[Twinrova]

You expect me to believe you are 4 only 41 with two college kids? Lmfao.

[Asker]

I had them at 19 and 21. I was a very young mom

[jmf909]

Just enjoy yourself dont over think it. keep it secret at work makes it more fun. be ready for break up and be mature about it know what i mean.

[Browneye57]

The term 'fuktard' comes to mind. WTF are you thinking?
Worse, he'll NEVER be your equal. EVER. He's called a 'boy-toy'.
You're a sick woman.

[cntrytbm]

@Browneye57

I tend to not take the advice of anybody whose alias is similar to butthole. Of course you think the world is shitty if you only see it through your browneye (aka ass).

[Nachowedgie]

@cntrytbm You're not the asker

[cntrytbm]

@Nachowedgie Nope. But if I was, I would ignore ignorance like this. I'm assuming browneye is your butt buddy?

[Nachowedgie]

@cntrytbm No I've never seen him before. Using homosexuality as a form of insult is pretty homophobic of you though

[Browneye57]

@cntrytbm - The term 'cunt' comes to mind. Fuck off asshole.

[cntrytbm]

@Browneye57
Yeah buddy, further proving you're not intelligent enough to hold a real conversation.

[Browneye57]

@cntrytbm - Ah, another 'all that AND a bag of chips'. Urine. As in, urine idiot.
If you don't care for adult conversation then just move along. No one has time for your drivel. Or block me, or I can block you. There's no connection. AT ALL.

A 40yo fucking a 20yo at the office is despicable. Sure he likes it, who wouldn't. But she should know better. That you fail to recognize this is a complete failure on your part. Now fuck off and go bother someone else.

[cntrytbm]

@Browneye57 poor lonely old bitter man.
You need to find some happiness in your life my friend.

[Nachowedgie]

@cntrytbm You're adding literally nothing to the conversation

[Browneye57]

@cntrytbm - You really are dense aren't you? I'm as happy as they come, a full live, thirty years with my beloved, three grown children, all the success one could hope for. But here you are judging based on replies to your stupid comments. How bout FUCK OFF YOU IDIOT.

[sweetpeachkiss]

well i mean i'm still a teen but i'm datin someone dat is 17 about to be 18 in January so... and i really kinda dont kno what to cause i'm 15 so... yea

[venomhbk1313]

You should be happy that you have someone and if you are happy that's all that counts don't worry about keeping it a secret if people give you shit about it screw them

[Guanfei]

You're both grow ups, that's no big deal. The issue is that if he gets any promotion, or raise, or advantage, people will said it's because you sleep with him, and not because he deserves it.

[Waz2020]

Well that's great, but if he goes for a promotion and is successful, you'll want to hope none of the unsuccessful applicants find out, besides with him being younger, if he finds a "newer model" what then... you sack him?

[OddBeMe]

Try to get him out of your supervision would be the best thing. If HR found out now, you'd have lots to answer.

[codyccc]

Obviously you use your position to promote him to your level so you're no longer his boss

[fred_durst]

sounds so fake , this question is surely made by a guy who make pink account and watch porn too often

[Anonymous]

What if he is using you for his benefits? Try asking him to find another job and see his reaction.

[Asker]

I actually have. He's agreed that if another job comes up then switching would be the best choice. However in this job climate he hasn't been able to find anything. Until he finds something (which could be soon, but could be a long while from now) we're still in this predicament.

[Asker]

I'd still have concerns about the age gap regardless. However, if he gets another job the "could lose our jobs" problem would go away

[ConstantPain]

Stop sleeping with him whore! you don't sleep with your employees. You disgust me

[sweetpeachkiss]

lol dang dat is disgustin eww

[ConstantPain]

I know right

[sweetpeachkiss]

first of all why the hell do you wanna sleep wit your employee dats like sayin you wanna sleep wit a stipper and wtf dont ever do dat either lawwd

[SwordShield]

Honestly, stay in a relationship with him. It sounds like you guys are made for each other.

[not329446]

Drop the dick and get back to business. Play time is over.

[asshole_]

He's a prostitute, or an escort. You're paying him, for sex

[pervertedjester]

One of you needs to quit.

[Anonymous]

Stop seeing him outside of the office and move on quickly.

[Asker]

Are you saying I should keep seeing him (just not in the office) or are you saying I should quit seeing him entirely?

[Opinion Owner]

No, you should stop this relationship completely. This is inappropriate and you could have problems.

[Asker]

I know, but I do feel something with him that I feel with almost no one else. There have been a few times I've tried to stop the relationship because 1) I know I shouldn't be dating my employee 2) I know he's probably too young for me. However, I've always gotten back really quick because I get super sad when we break up. I always have ended up getting back with him because I am so extraordinarily pulled towards him and being with him makes me incredibly happy. (but on the flip side I do realize the relationship is inappropriate, which is why I'm torn)

[Asker]

I'm not sure I can stop seeing him because I have such strong feelings for him. I realize it's inappropriate (he's way too young and he's my employee) , but I don't connect with men like this pretty much ever

[Opinion Owner]

I do understand. However, this relationship seems pretty much doomed. It's better to end it right now before it get even deeper and more complicated.

[Asker]

Part of me thinks you may be right, but part of me thinks there could be a real chance. I know he's a lot younger, but I don't feel an age difference with him. He's very mature. Moreover, I've connected with him in a way I connected with almost no one ever (including men my age).
I know the "him being my employee" thing is a big risk for our jobs, but we do keep it pretty well hidden at work. We don't have sex at work. We save that for after work.

Is there any other reason you might think it's doomed to fail? I'm really trying to think this through and therefore look at it from all angles. There may have been something I haven't thought of yet.

[Asker]

Also, do you think it could still work despite the age difference and him being my employee?

[Opinion Owner]

I've dated a younger guy before. It was meant to end. Most relationships aren't made to last overall. The more differences or obstacles (such as a large age gap) increase the risk. Plus, you don't feel the difference now, but how would it be in 5 years, 10 years? Many young men like older women. However, the older a man get, the more he's likely to want a younger partner. I guess I wouldn't be so trusting. Adding to that he's your employee. What could happen if he decided to tell people? This is a risky situation to me.

[Crowejerms]

If hav sex In tha sky or eat ot whilebu hanging off tha rug

[Aphrodite_1998]

Nothing wrong maybe if he get the other job kept going but be honest with him.

[abc3643]

Help him get a job with another company.

[Asker]

I would, but 1) it's super hard for him to find another job in this condition and 2) this job is a huge opportunity for him and I don't want to take that away from him. I'd feel really guilty and selfish if I pushed him down that route.

[DavidHart]

Allow me to say this.

FIGHT FOR YOUR LOVE.

[Asker]

How specifically do you think I should do that given the circumstances?

[DavidHart]

Just continue doing what are u have been doing,
such as keeping it a secret from current job.
.. which makes me wonder if there's any policy in the company which is prohibiting relationship between employee from the same department..

That’s my comment for job alone.

[ButtaGrey]

Sorry but no amount of ass is worth my career.

[MannMitAntworten]

Why does the age gap bother you so much?

[GreenGold1992]

This sounds like my ultimate fantasy

[Janenow]

Follow me

[GreenGold1992]

@Janenow Just did

[thruholewizard]

change jobs and enjoy him !

[Anonymous]

Yo he- he’s tryna get that raise lol

[CheeseBurgah]

lust is a strong feeling

[Nachowedgie]

You're a piece of shit

[Jmmmfi4]

Just have your dirty secret. This is so hot.