Dating my boss.... its gone bad... I want to fix it if possible. Please help!

Will keep it brief as possible, thanks for reading, please leave advice, the common answer will probably be the right one.

Me(29), her(26), me p/t DJ at a bar, her, the manager of the venue.

She's was in a mess of a relationship and when I started my sat night job we got chatting. We get on well and we chat a fair bit. It turns out this guy is her boyfriend of 18 months and best friend previous to that for like 6 years... he's massive in her life, but it wasn't working, they never saw each other, they argued a lot (his ex, her former friend doesn't know of them)... basically its a mess and even as a mate I adviced her to get out.

Then one day she comes over to chill and one thing leads to another. That was a month ago... in that month we've stayed with each other like 20 times, she tells the guy its over about a week in (yes, not great, I know... ). She's gutted, but says its for the best and we have a really good 2/3 weeks.

Last Friday is a gig they have tickets for, his christmas present. We chat and decide if they want to stay mates its only fair to let him come and see the gig (he lives like 2 hrs drive away). I'm not overly happy, but given who he is I see the point and agree.

I see her saturday, she seems ok, I ask her about the night she said it was "emotional", but that's it.

Then I get a text as a reply stating "I'm so sorry, I'm so confused, I don't know what to think or what to do. I really care about you, your amazing, but my head is a total mess and I don't want to hurt you" ... I'm gutted

We ring and I say I understand where she is coming from, he has been massive in her life. I get the impression its honest confusion and guilt and sadness and being a mess. Not that I'm being played or anything. I put out there that I will give her space, no contact for a few days (bearing in mind we've seen each other like everyday more or less, very full on) and we'll meet up thursday to talk.

As a bit more background, I really think she honestly felt or feels for me. She invited me to weddings in april and june, she shared a lot about her family and such. She's a private person and was very open with me. I think our time was genuine. But I know (some) of how important this guy has been/is.


1) what do you do if you were me? how do you handle this? What approach do you take Thursday.

2) Keeping my job is important, seeing her won't be fun if we split, but I really need the income, I'm in a lot of debt... How do I try to keep it?

Thank you for reading this, I know it wasn't short. Any and all advice is very welcome. I've not a lot of people to talk to. All my mates are manly men, not exactly sharers.

Hey all, thanks for the feedback and help, many of the comments have been very kind and insightful. So we've not exactly managed to do the no contact thing and the meet up is tonight. We'll see how it goes. Fingers crossed and thank you! :-)
So I get a text on Monday evening telling me she's found a house (is trying to rent, but has a dog so V difficult. The thing is the house is like 45 seconds from my place... good be good or really rubbish. I wish her luck
i wake up on Tuesday to a 3am text saying "i miss you". She goes to the next city to have a drink with a friend and after some wine I get "i miss you, I need your hugs" as a message. She rings at like 1am to hear my voice...
She comes over at 9am Tuesday morning with breakfast, we hug, we don't talk, its very nice, we're just silent together... I hear nothing from her since this. her FB status last night was "is deeply confused"... am seeing her tonight.. :-/ will let you kn
i meant she comes over Wednesday morning... basically I think she's missing me but is v confused, this guy is huge in her past and she doesn't know what to do. once again, thank you for your help. will let you know how it goes


Most Helpful Guy

  • The best thing in your favor is time. A couple of weeks, or months will sort things out and the less you do the better your chance of keeping your job, and maybe winning her back. She needs to see what a sane boyfriend looks like.. try to look like that.

    It sounds like she has a ton of drama and things need to follow their course. But if she tries to start things up again, try to make sure she has completely ended her relationship with the other guy, or you will be back in the same boat in a few more months.

    Good Luck,



Have an opinion?

What Girls Said 6

  • I would just stop talking to her until she makes up her mind. She needs to stop all contact with the ex before moving on with you because right now I Feel like she's not respecting you enough.

    2. I think that keeping your job is good, either way, stay friends and your job should not be determined by the status of a relationship. You can always go talk to HR management if she discriminates you for a stupid reason such as 'breaking up'. you're both adults and adults date, that's normal. If she's in a position to fire you for personal reasons, that is against workplace laws actually-if it was due to inefficiency at work or something like that, then termination of work ensuing would be valid but she doesn't have the authority to just fire you if you break up with her. That would look quite foolish on her part.

  • I think there is a simple and respectful way to approach this...Were I you I would back away...Tell her that you think it's best that you two not be in a relationship just now because you feel it's causing her more grief than she is already in...She will say, "No, I don't want it that way", (paraphrase there) which you can reply, this doesn't have to permanent, it's just necessary right now...Because if a relationship were to evolve at this time, it's a relationship that blossomed out of a negative situation and will likely interfere with your relationship in a negative and likely destructive way...So it's best to wait for a time when there aren't these kinds of obstacles and dramas in the way... That type of approach will not disrespect her, you can keep your job and your friendship...Best of luck. Cheers!

  • she needs time. she was with this guy for awhile. she obviously needs time to get over him. she's obviously torn between whether she wants to be with him orr not. it seems like she does but she's not sure if it will work. I would rreally just be her friend at this time. that's what she needs most right now. maybe in time she'll want to be with you but I think that if you want to be with her right now is NOT the time. the probability of you 2 worrking out right now is slim to none. if you give her time to be single and get over this guy and THEN start something up it is more likely to work out. good luck. and I agree she doesn't mean to "play" you she seems to be honestly sorry.

    • I don't know about that.... he's already slept with her... taking a trip to friend-ville doesn't seem like a good idea... cause he'd probably STAY there. Just play it cool & give her whatever she needs...

    • Giving her what she needs will put him in the friend zone because he's being her bitch and putting up with anything. he needs to be there but set boundaries so she knows she can have him but not if she's not over this guy

  • I'm just wondering how big a disaster this will finally turn into unless you get out of her life immediately,

  • First of all she needs to know what she wants. Until then it would be a bad idea to talk to her outside of work. If she doesn't know what she wants you will like keep feeling hurt in some way. I don't care how much that other guy is in her life; she still needs to make a choice. Until she knows what she wants you should back off; cause boss or not its not kewl to keep getting stringed a long like that.

  • Go on with your job and don't think about the situation, try to think about the music at work. There are different exercises and ways of canceling out the negative energy. If you still have trouble, you'll just look to take your sounds elsewhere. Just learn from this "experience".


What Guys Said 13

  • Well, this is one reason why dating in the office is not usually a good idea... unfortunately...

    But, that's not what you asked so I won't harp on it.

    This guy is obviously very important to her, even if their relationship didn't work out. She's not gonna get over him quickly and especially not if she's still hanging out with the guy as a friend.

    1 - Be as casual as possible, the cool/unintimidated guy is going to be a real turn on for her. If she decides to get back with her ex... just let it happen, because you can't stop it anyway. If she wants to stay with you, hey, that's great, keep her.

    2 - As long as you don't have a "bad breakup" you should be fine. I've stayed friends with all my ex-gfs, it really isn't that hard, unless you are a jerk.

    If she stays dating you, you've got nothing to worry about.

    If she goes back to her ex & you let her, you got nothing to worry about.

    If she goes back to her ex & you try to fight for her, it could get messy & then you've got problems...

    Basically, sounds like you've got a good shot at keeping her, but she's confused & needs to figure out what she really wants. It sucks but your best bet is to stay cool & wait it out... she'll figure out what she wants.

    If she left that guy for you & you're understanding & cool... odds are good she'll figure out she wants you.

  • Tough situation you have here.

    Personally, It seems to me like you are the, "Back-up Plan". Shoulder to cry on, best way to get over someone is to get under someone else, fill some void in my life...

    Make matters worse, she's your boss. You can't make waves, you need the job.

    Well, if this was me, Come Thursday, I'd be busy. No little chat, No coffee, NO walk in the park.

    Let her see that she can't have her cake and eat it too. If you care about me and you care about him and you are so confused, then you certainly need time away from me to make up your mind. If it's him, so be it. If it's me, some HEAVY convincing will be required.

    Dude, Thursday if she's interested in your chat, tell her, oh I'm sorry, I made plans to take someone out to lunch or dinner or whatever. Tell her, may-be next thursday, if things don't go well with this girl I'm seeing thursday. I'll bet you Dimes to Donuts that she'll make up her mind really quick. But, if you stick around and be there for her and let her feel it's ok... She won't make up her mind.

  • she jumped onto you too fast...respect her and give her the space you need

    as far as thursday, just be cool, clam, show her you listen to her and will respect her decision either way, I mean you haven't even dated that long so you shouldnt be too emotionally attached - although I undertand if you are...but youve got to look out for yourself and your job, don't be a d***, play it cool and be mature, show her you respect her wishes...

    hate to say this but you sound like a rebounce aka someone who takes the persons mind off their ex, or at least that's the point of a rebound lol...see what I'm saying? I know it sucks but its what it sounds like...who knows if its meant to be it will be...dont push for anything, let her get across what she wants right now and respect whatever she says, don't cry or be dramatic just be yourself man, especially since she's your boss you don't want to end things badly

    as far as seeing her around while ur DJing bro that shouldnt matter...girls should flock to you, you got all the music, up to date with everything that's coming out, girls like that stuff...i mean you're at a place where people go to have a good time - it shouldnt be hard to find someone else even tho ur heart may not want to right away - take ur time, don't jump into anything like it seems she did...

    hope this helps - stay cool

  • Well, I think you need to be straight up about things. Your job definitely needs to be brought up.

    Just be understanding, and make yourself out to be a pretty chill, relaxed nice guy (you sound like one so that shouldn't be too hard) who thinks she should do what's best.

    After you make it clear that you two will be ok (even if on your end it isn't, its a white lie to keep your job and maybe even get a second chance with her, because I am sure the main reason it fell apart was that it was way too soon) bring up your job. The big thing here is NOT to guilt trip. No one likes feeling pressured into making a choice. Just say something like that there won't be any incidents from you at work, you can separate personal and professional, and that you would love to continue working if its alright. Saying something like that will make her have the urge to match you in professionalism (humans are naturally competitive) so she will let you keep your job in order to be just as mature about it as you.

    The situation sucks, but good luck on Thursday!

  • Since you still have to work with the woman and you need the job, take things easy on Thursday. If she's still confused, just do what you've been doing and let her know that you will give her the space she needs to sort things out. And that while you want to be serious with her, that you'll understand if she wants to slow things down and just be friends.

    You need the income that this job provides, so even if she wants to break up with you, you have to keep things cordial. You have to keep her feeling comfortable working with you. Whatever choice she makes, you can't get upset by what she chooses. You just have to accept the decision for what it is.

  • The boat is over weighted by outside DRAMA, the way I see it, only two things you can do:

    1. You can get out the boat and swim to shore, save her and save your self. Or...

    2. You can lay anchor and pray she sorts out, and saves you both. Or...

    3. YOU BOAT DROWN! =)

    Not the best answer, but you said it yourself, it's going to be hard seeing her around. If you two were to split, so I assume your hoping she chooses you over him. But at this point in time, it's her decision.

  • wow.. you broke the most important rule. you don't sh*t where you eat. start look for a new job then theeher you need to know what the deel is with the 2 of you u may need to resign or runn the risk of being terminated whll your the screw and she is the drill

    • That is an important rule, but there are exceptions to that rule.

    • Few exceptions to that rule. Any and all relationships bring drama at some point in time. I always say, Business over Pleasure.

  • I'd get as far away from her as possible, as soon as possible. Emotionally, evenif not physically given the job. I've had this problem...when will we learn?

  • sorry I just took a massive bong hit before reading this, and its hard to help with something like this with such good weed, I wish I could help though.

  • Dating + Job + Co-woker = No No!

    Added BONUS... Boss = Double Negative and big NO NO!

  • You used her it was fun now you are worried about the job. If she really was important to you, you wouldn't care about the job, get another one...

    • How did I use her? people fall for each other. The fact your posting anonymously shows that you know your being a prat. The job pays bloody well and getting a new one would not be easy. Go play with traffic you tit

  • Should have thought about all of these things before you decided to put it in her, but the blood was somewhere else, its one of the rules don't do anyone at work, and you even went further, an emotinally unstable boss, who I am sure is older and mature enough not to act out and get rid of you if she feels oh I don't know a little emotinal and upset, live and learn try and get the best possible outcome under the circumstances...its funny becasue its not happening to me..

    • The reason you did this anonymous is that you know you know your an idiot... and now we can add coward. your a waste of a person dude! congrats, no matter how sh*t live gets, at least I'm not you! Hope live is crappy man, hope its very very crappy!!!!!

  • You are screweeeed...