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Sunday Confessional: Sleeping With My Manager

This week's confessional comes from our anonymous Confession Booth group in the TrèsSugar Community. Feel free to offer your advice in the comments.

After flirting for months, I am now sleeping with my manager. We get along great and I would love to explore the possibility of a relationship with him, but we only get together after happy hours or work events. No one at work knows. Am I making a big mistake?

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nomorecoffee nomorecoffee 7 years
you guys are going to end up in court
bittie bittie 7 years
yup, mistake. you said yourself he only wants to see you when you're already out together and drinking heavily. soooooo, unless you are comfortable with no-strings-attached, convenience-based, socially-lubricated hook-ups and not a single thing more, sounds like you're going to end up getting hurt.
PinkNC PinkNC 7 years
If you’re going to be in a real relationship then just say it to each other and then be in one. But if not, then get out of this situation now. Back away from it before it conflicts with your job and one of you has to leave it, or get fired because you can no longer work together.
LeftosDotCom LeftosDotCom 7 years
This is a very complicating dilemma. At first the average person would say, "terrible idea" but then again everyone's heard of someone who married their boss or coworker and then it makes you wonder. We had a couple users on our site discuss the topic here. Not all bad (one girl got married) but not all good (one girls relationship ended because of work) - - You may want to consider asking it again and giving some details to your personal story so you can get answers that are specific to your situation.
Yogaforlife Yogaforlife 7 years
I would question how serious you are about your current job before you pursue this further. If this is a job you really don't care much for, then by all means, have your fun. If you hope to advance at this place of employment, I would not pursue it further and would put a stop to the interactions. This is not good for your career, especially since he is your boss. I know lots of people who have met and married people they work with, but usually it involves dating and not just sex after work events, and they often work or end up working in different departments to avoid conflicts of interest. Just be prepared for office gossip and know what you plan on doing if it goes sour.
runningesq runningesq 7 years
Yeah, I highly doubt no one at work knows.
medenginer medenginer 7 years
I'm sure most of your co-workers aren't as naive as you think they are especially if the flirting has been for months. I'm not sure he's ready for a relationship considering both of you don't be seen out in public. I would find out if someone else is in the picture or what's going on because his schedule sounds questionable. If you pursue a relationship you might switch departments so no one gets into trouble.
janneth janneth 7 years
Oops. U forgot to go on a date first.
bluestar bluestar 7 years
If you want a relationship, then yes, it is a mistake. It seems like you are really convenient for him.
bellavita214 bellavita214 7 years
If he wasn't your boss would you sleep with him? The answer to that might let you know if it is a good idea or not.
xgreenfairyx xgreenfairyx 7 years
It happens all the time. Use common sense. Have fun.
chloe-bella chloe-bella 7 years
I'm an employment law attorney, and I can say that these situations are frequently a recipe for disaster. It's one thing when someone is involved with a co-worker but another thing when they're involved with someone who has managerial authority over them. Also, if you're already sleeping with him and he doesn't have any interest in spending time with you outside of work happy hours, then it's probably not going to go anywhere.
Ac2366 Ac2366 7 years
People at work probably do know. I think it's a mistake and I wouldn't risk my job. Things could turn awkward if it doesn't work out.
jazzytummy jazzytummy 7 years
Yes, it is a mistake.
mndmay mndmay 7 years
My first thought was: Is he married? If so, that answers the question. Otherwise, talk to him about it.
jenni5 jenni5 7 years
It could work...I met my hubby at work. But like others said be prepared for it to be super awkward if it doesn't work out. And when people do find out, and they will, you WILL be the office gossip.
gigilgirl gigilgirl 7 years
I think it's alright. Make sure he's not married though :))
notinthemood notinthemood 7 years
I think it's a mistake. You want more out of it... what if he doesn't? How are you going to feel at your job when/if you're dumped? There are just too many bad things that could come out of it that I personally wouldn't want to deal with. That, and depending on your company, he could lose his job for sleeping with people who work under him.
Pistil Pistil 7 years
I'm not saying it's a mistake, but it sounds like a convenient arrangement (for him) and I don't know if I would count on it becoming anything more. I guess you could try, but be prepared for the awkwardness that might ensue should this relationship ever go sour. Do you like your job?
tlsgirl tlsgirl 7 years
Not necessarily. I think it depends on what you both want - you said you only get together after work events or happy hours, but is that because it's convenient or because he hasn't expressed an interest in more traditional dates? If you're both into it though, I would say go for it. Yeah, work stuff can get awkward, but you just have to set some boundaries. After all, tons of couples met at work - it's where we spend most of our time.
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