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...

[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.

[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

[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.