A
female
age
36-40,
anonymous
writes:I don't know where to even start with this. I am falling for my boss. But first lets start with this: My boss introduced me to his best friend. Whom I dated for a year, then things started to go bad. He had a temper that I just couldn't get past. I talked to my boss all about this, and he told me to leave his friend. Then his friend went balistic, he yelled at me told me I was a horrible person and basically made me out to be a crazy bitch. I wasn't going to deal with it anymore and told him we were done for good. Suddenly he decided that I wasn't to blame anymore. Now it was his friend's fault, my boss. He was just a terrible friend, accused him of being on all sorts of drugs and threatened my boss as a father. Needless to say, my boss had enough of him. He for the most part has swarn my ex off as a friend. Through all of this my boss has been there for me. We talk all the time, about everything. I really couldn't ask for a better friend from him. I guess that's why I'm falling for him. But it's torturing me to see him everyday and not be able to tell him how I feel. I am planning on leaving my job very soon. I need a change from my life. I've already applied for new jobs. My question is, because of everything my boss and I have been through together. Do I tell him how I feel? I won't tell him anything until I resign. He flirts with me all the time. I do believe he feels something for me. But I don't know if it's worth risking the friendship we have. So should I tell him? Or just leave and hope I don't regret it later?
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best friend, drugs, flirt, my boss, my ex Reply to this Question
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female
reader, anonymous, writes (25 July 2010): Thanks for the advice. I will definately wait until I find a different job before I tell him how I feel. I know that regardless of how he feels, he will still maintain a professional relationship with me. Aka, still give me a good reference if I need it. He is truly one of the best guys I have ever met. I'm hoping to have everything figured out in the next couple weeks. Oh, and yes he is single.
A
female
reader, DrPsych  +, writes (24 July 2010):
 I don't think you should act on your feelings until you have secured alternative employment. You wouldn't be on an equal footing to your boss if you dated him while you remained in the job since he would be in a position of power and authority over you in the workplace. You don't mention if your boss is in a relationship or marriage situation. If he is, steer well clear no matter how you feel. If he is a single man then there is no reason why you cannot raise the subject of romance after you have resigned. Arrange to go out for a drink with him as part of your leaving party. Having left the job it won't be embarrassing if he declines the relationship you want because you won't have to see him again. However, get the job and reference out of the way first!
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A
female
reader, missdimples3 +, writes (24 July 2010):
 After you do leave your job I say you tell him exactly how you feel... he might just feel the same for you :) don't let it pass you by. live with no regrets. good luck x
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