Should I reciprocate the interest of my boss?

[Anonymous]

He's the associate director in my company and basically heads multiple departments here. He's like 30 years old. I've always found him cool, he's very flamboyant and has an impressive personality. But I obviously never ever thought of getting into any kind of relationship with him.

Lately he's been showing interest in me and although he hasn't done anything inappropriate, I feel he's open about his interest. In our company, multiple people are dating or are married in the departments over here. So the HR doesn't have any issue with that.

However, I'm a bit concerned about what people would think. How they would view me or him? I think he's not concerned about that at all.

Updates

1 y

I've also never ever heard anything negative about him since I joined over here. People are always praising him and he's not sleazy or anything very respectful and polite towards everyone whether male or female employees.

[Finchie40]

Never mix business with pleasure , unless you don’t really care about your job and don’t mind the consequences that could occur, if things don’t work out between you and him. Yes people will talk and gossip about the 2 of you , so these are things you should really think about before pursuing your boss. These type of affairs occur a lot in the workplace because you are seeing this person on a regular basis , giving you more time to get to know each other. So if he is showing interest in you and you really like this guy then yes go for it if you don’t really care about your job , but if you do care about your job , you are best not to move forward with him. Also really ask yourself if you are really attracted to him or are you only attracted to him because of his job status? Put him in a janitor outfit and no longer your boss , would you still date him if that was the case?

[Asker]

I'm not a gold digger. As I said, I've always thought he has an impressive personality and I think I would be attracted to him even if he wasn't the director even if he was just my manager or a teammate, I would still feel the same way. He has a lot of gravitas, his personality is just like that. He would shine anywhere.

[Finchie40]

Then go for it , if you feel that type of connection with him , I have hooked up with girls’ from work before , only if her and I have a great connection with each other after we got to know each other for awhile , so if you feel that type of connection with him then Go for it

[ManOnFire]

@Finchie40 Terrific answer.

[ManOnFire]

As I've noted on this site before, male bosses are always going after female employees they find physically attractive. That does not equate to it being a good possible relationship, and more often than not their attraction to you is highly sexual without even really knowing you as a person to be able to say they actually love or care about you.

Often times these guys are already married and will either leave their wives for you, or at least cheat with you on the side. And they can and do flip the script and end the relationship with you to go back to their wives. I know some workplace stories that would make you sick.

Regardless of how many situationships go on at your job and whether HR knows about them or not, it doesn't mean you have to do the same thing. In my opinion it's best to stay out of that kind of situation and seek your lover outside of work.

[SweetJoyGirl]

Oh, hecc no

If it fails, you can kiss the job goodbye. Don’t date a coworker or their family member!

[Account]

Sure, if you want to risk destroying your career, go for it.

[Account]

We are not even talking about a coworker. We are talking about your boss. Wake up, girl, life isn't a drama series.

[lightbulb27]

messy. if it goes wrong, you gonna back stab him or him you? Will you sue the company for millions? If goes wrong, how you gonna work for him... can you be adults and do your job being paid for while you each date others?

Will others be jealous and sue company because he favored you over them... maybe discrimination lawsuits? Will others question your promotions and favoritism, real or imagined? What kind of back talking will there be and can you handle that? Are you professional enough to handle this?

or will it work out and you get married?

it creates a social mess.

If you do, then I'd make it open and clear somehow and be clear about how he is being fair to others. I know someone whom is dating their boss with a wider age gap than yours. they are open about it in the company and so far hasn't blow to bits.

[CuriousHubby]

Your screwed either way. If the people care owells but he will care. Your either going to date him and get promoted and if it ends badly fired!

Be a good digger and if he leaves your screwed and hated.

Really just be nice friendly and soft tease till you get promoted 😉. All women do this or go beyond and dare him till it goes south getting greedy for more.

Get evidence for HR and keep it giving them hints he is on the line constantly. Get his affection but not date and promoted and when he shoves you to date say it's not appropriate and tell her for protection from being demoted.

[ProbablyClueless]

This is just my personal approach to things, but I think you would be absolutely insane to mix personal and professional relationships like that.

Regardless of what anyone else thinks (your coworkers won't think anything good), workplace relationships get so messy the instant there's any problems.

[Twalli]

Don't date coworkers and definitely don't date superiors. It's not a matter of company policy, but just about a healthy relationship.
1) If you have a fight then you can't go to work to cool off, because you are working together. Therefore, you don't have time to cool off after a fight.
2) Because you're in a relationship with him, your superior may treat you differently.

[normalice]

I would bet he just wants to use you and sadly there is no way to check because he is your boss.

[Asker]

Why would you think he just wants to use me?

[Asker]

Like I said he hasn't done anything inappropriate

[normalice]

This has happened before. Many times.

[Asker]

Yes but you can easily judge that. Sleaze bags are easy to spot.

[normalice]

Yeah, men have adjusted to new boundaries but their goal hasn't shifted,

[normalice]

The sort of sleaze bag that gets promoted to such a centralized position of control tends to be very good at hiding their sleaziness - even often from themselves.

But I'm not saying he is. I'm only trying to emphasize that there is no way to know other than taking the plunge and finding out the hard way. If it's worth the risk to you by all means do it.

[Asker]

I'm not taking his side, but this is my second company. In my previous company, people knew exactly which HODs were sleaze bags because you can't hide your personality for long.

[normalice]

It is true that with sleaziness tends to come too little self awareness to hide it but this doesn't apply to the sort of true sociopaths that tend to rise above the normal sleaze balls.

[OddBeMe]

It does help to imintate those you wish to impress. In business meetings I adopt their posture and opinions. Which in Texas are rich conservatives that make me want to blow my brains out.

[noohair]

My father taught me a valuable lesson. Women where you work are off limits. No exceptions. I have seen men lose their careers over this.

[zagor]

My old boss started dating a subordinate and now they are retired with adult kids, so...

[RedInnocent69]

No, direct reports shouldn’t date thei supervisors. It creates a toxic culture.

[Anonymous]

Well, you said he’s flamboyant so he could be gay, it’s not a good idea to get involved with the boss though

[SugarSugarplum]

Never date a coworker.

[Nikki1989]

Don't poop where you eat.

[gag6474]

marry him. he's rich and kind

[Walksbehindtherows]

No. Be a good Christian

[ICanSmellTheCosmos]

Don't crap where you eat. Bad idea.