Should I ask my boss out?

[Anonymous]

Updates

2 mo

To expand, I haven’t been in a relationship in 2 years, and that’s what I want, not a hookup. There’s lots that we have in common, including not having nor wanting kids and that is especially hard to find where we live.
I can already tell my coworkers are nervous about me becoming the favorite. I want them and my boss to know that my job comes first. I just want to get to know him better but even the most casual conversations feel like we’re in a fishbowl - no privacy.

Updates

2 mo

Ultimately, I’m too new, so I’ll wait. It’s not a matter of ‘if’ but ‘how.’ I’m here for the male perspective. In any other situation I’d let him make the first move. Isn’t that what men still prefer? He’s a professional so I wouldn’t be surprised that he wouldn’t make the first move so that it wouldn’t be seen as taking advantage of his position of power.

Updates

2 mo

It’s been made clear we’re attracted to each other. And we understand that we both have a strong work ethic. So we’re putting our jobs first until one of us is ready to leave. We’re willing to wait for one another too. At least, I am, because I wasn’t looking to date now anyways. I don’t want to insult his sincerity but it’s too soon for me to know if I can believe him. Men have told me many things to sleep with me. But I appreciate taking time. Thank you everyone for your input!

[OneViewpoint]

If you really want to date this guy, get another job first. Dating your boss can create all sorts of problems in the workplace for both of you. You seem to understand that but you also seem to not want to accept it. And you're 45, kids are off the table for you whether you want them or not. You go on to say you're new at this job. I'm seeing a pattern of impulsive behavior.

[Asker]

Lots of my jobs have been contract work over the last decade, lasting a few weeks to a few years, depending on the project. This one is more open-ended but similar. Impulsively dating at work is indeed how I learned not too. This is just the first time I’ve been in a tiny town where it’s nearly inevitable. I just want to know him outside of work, which could happen as I go out more, but most of us at that job work long hours & go home.
I actually can have kids at this age. I’ve seen multiple doctors about it. And I love kids. But having one under 10 in my 50’s sounds exhausting.

[OneViewpoint]

Ah, the tiny town constraint is tough to overcome. Rules need to be tailored to the environment. In your case I’d say the other people you work with will understand the dating pool reality there. But…. The women will hate you even more for taking an attractive guy off the market. And everyone knows everyone else’s business. 🤣

[Asker]

Yeahhh, that’s what I’m really in denial about. Women here were so mean at first. I just wanted a friend and they just wanted to know my business. Now I laugh for sure.

[Theunfadeable]

if your boss has any brains, he avoid you because people are already noticing you like each other. Most companies Would fire him if they found out the Two of you were seeing each other. If you wanna ask him out, you may as well because there’s no real consequences for you as a subordinate but for him that would be one of the dumbest moves he can make.

[Anonymous]

Go for it! Does he own the company? If he does, no need to worry about HR getting mad.

[Opinion Owner]

I think it sounds like a fantastic idea. You just need to find some privacy to ask him.

[Asker]

lol, he doesn’t yet. But I can’t emphasize enough how small this town is and how impossible it is to not date your coworkers.

[Opinion Owner]

Go for it girl

[Telekinetic-Potato]

Big risk, big reward

[Opinion Owner]

@Telekinetic-Potato true…

[Opinion Owner]

Update: that’s great news! Hope it works out

[Asker]

Thanks! Your responses have been way better than all the negativity. And while I didn’t exactly ask him out, I just directly told jim I was attracted to him, and it’s up to him for where that goes.

[Opinion Owner]

Awesome!!!

[Nikki1989]

If you want to take that gamble, sure thing!

[bobalife]

Unpopular opinion, small town, why not if the vibe is there at your age?
Tbh I know someone who got with her boss and just married lol. I never asked how they managed it at work before she quit, but they made it work 🤷🏼‍♀️

[Asker]

I’m liking this. I’ll definitely feel it out more first. If it’s meant to be I don’t mind playing the long game.

[Screenwriter]

If this guy is a professional, it's more than likely he would know what a minefield he'd be entering by dating or being in a relationship with an employee. And if the relationship sours it could mean you'd lose your job. Since he hasn't asked you out, I'd think that's an indication he isn't willing to put the employer/boss relationship or the boss/c0-workers relationships in jeopardy.

I think it'd be safer and more rational to fish in another pond.

[molonski2]

I think you have summed it up well ,
Yes , sure ask him out , just wait for correct time , worry about the other stuff when it works out.

[Staximus]

Which one do you need more, the job or the relationship? Being in a relationship and working with somebody is a real test. If the relationship goes bad then you’ll be looking for a new job.

[beenherebefore]

No, I think you should keep things strictly professional at work instead of mixing personal life and work life. If your job comes first as you say you shouldn't be looking for potential partners at work and just do your job instead.

[beefcakebradybatson]

Don't know if that's wise because of the workplace hierarchy.

[Master_Debator]

If you already had sex with him... sure. If not, you're messing with your job.

[Asker]

Oh lordy, I definitely prefer to date and not have casual sex.

[slatyb]

No, you to should not. It's unethical for managers to date someone who reports to them, directly or indirectly, and most companies forbid it.

[Iron_Man]

Were you pink anonymous just asking this question not too long ago

[Asker]

Yes. I accidentally posted it twice.

[Asker]

Dropping this here because I didn’t know I had a limit on updates on this site:

And I’m almost certain he likes me. He has a hard time making eye contact with me, but no one else. He quickly turns away whenever we accidentally touch hands. And he gets giddy (no other way to say it) with his staff after I praise his work. That part is easy; I’m not even flirting, I just admire and appreciate what he does. Being friendly and personable is part of my job. But I want him to know I like him and am not just treating him like I do everyone else.

[888theGreat]

NO , if you like your job. Also any benefit you get after and all your co workers will hate you , talk about you , not work with you.

[Asker]

Ugh, I do like my job. That’s the other downside of being in a small town; few to choose from and I want to keep this one.

[MrChinaski]

Coworkers is difficult by navigable. Boss? No, you need to leave that job if you do.

[Texaskid1]

NO.

[Anonymous]

I think it's fine, but not everyone will. If you do, just make sure you're very clear that if he's not interested, work will continue entirely unchanged.

[msc545]

No, don't get personally involved with people you work in with and particularly not with your boss. Not if you value your job.

[RedInnocent69]

No, not your boss, unless you’re prepared to change jobs

[Dantezam]

Well, that can either result in an amazing experience or the awkwardness if things don't work out

[Anonymous]

No wonder your unmarried another workalochlic woman with no heart. Smh, waste of life.

[Anonymous]

Yass Queen!! And if it goes south, accuse him of sexual harassment and get a settlement.😆

[StephanieChick111]

Go for it. Flirt with him until he gets it.

[jazzy34]

No. Inappropriate and unprofessional.

[exitseven]

No, it will create a lot of problems

[dudeinohio]

Not a good idea to date a boss.

[Zionne]

oh wow... if you think so

[Jeff51]

No. At the end it won't work

[Iron_Man]

Yes sure why not

[Anonymous]

Sure, if you like your boss.

[whosnumber_1]

Do it!

[whosnumber_1]

I would do it in a setting outside of work. Do you think he is attracted to you as well?

[Asker]

I think so. I married young and stayed married for most of my adult life. I’ve dated since but I still have a hard time telling if someone likes me. As in, actually likes me. I look almost half my age and a lot of men find me attractive but are rarely serious. As a guy, what do you think of this?

He has a hard time making eye contact with me, but no one else. He quickly turns away whenever we accidentally touch hands. And he gets giddy (no other way to say it) with his staff after I praise his work. That part is easy; I’m not even flirting, I just admire and appreciate what he does. Being friendly and personable is part of my job. But I want him to know I like him and am not just treating him like I do everyone else.

[whosnumber_1]

I have never been one to shy away from a live interest regardless of the setting. But in your case I would just be tackfull about how you pursue it. And probably be aware that it it doesn't work out the situation might be difficult. It's like have an emotional exit strategy

[Asker]

Thank you. Everyone has spoken the truth I don’t want to hear. But it can happen! I’ll play the long game. Prove my commitment to the job first, take the time at work to get to know more about him (as limited as that may be) and start off as friends. If dating doesn’t work out, I’m still excited to help elevate the company. It’s why he hired me. It would just be nice to be a dynamic duo in both arenas.

[oldman26]

Go for it