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Should I ask my ex-boss out?

Updated on: 29 June,2024 06:51 AM IST  |  Mumbai
Dr Love | mailbag@mid-day.com

If he thinks it’s over, and isn’t willing to commit to fixing it, nothing you do or say can help. Relationships only work when both partners want it to happen

Should I ask my ex-boss out?

Illustration/Uday Mohite

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I worked at an office for two years and had a huge crush on my boss right through that period. He is three years older than I am and we had a great rapport, but I never said a word to him about my feelings because I was worried about how it would be interpreted. I also didn’t want to make things awkward at work even though I sometimes suspected that he liked me, too. We were both single so it wouldn’t have been a problem, but neither of us said anything so I have no way of knowing how he felt about me. I quit the job two months ago and have been thinking of asking him out. I don’t know if this is a good idea because, if he refuses, it may ruin a professional relationship. What should I do?
You waited two years to tell him how you felt, which is awful given how short life is. Professional relationships come and go but personal connections are rare. If he turns you down, you will have the satisfaction of knowing that you were honest about how you felt. To assume the worst and give up on a potential relationship will only lead to regret in the future. All you have to do is ask him out for coffee and gauge how that goes. You have nothing to lose, and to assume that this will ruin your relationship as a professional is to do him a disservice because adults can be mature when they want to be.


Should I believe my boyfriend who thinks this relationship is over even though I don’t think it is? I believe he is just giving up too early and I can get him to change his mind. The question is, should I try if he isn’t willing to do his part?
If he thinks it’s over, and isn’t willing to commit to fixing it, nothing you do or say can help. Relationships only work when both partners want it to happen.


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