Should I date my friend’s ex?

Illustration/Uday Mohite

My best friend recently broke up with his girlfriend, who has been texting me since. I don't know how to react because I know he loved her a lot and was heartbroken when the relationship didn't work out. She says she has always liked me, and wants to get to know me better, but I don't know how my friend will be okay with this. I think one of the reasons their relationship failed is because she was always more interested in me, and I didn't say a word about that to my friend to avoid hurting his feelings. I would love to get to know her because I have always had feelings for her, but I know that doing this will damage my friendship forever. What should I do?
You had an opportunity to speak earlier and chose not to because you say you wanted to protect your friend's feelings. To spend time with his ex-girlfriend will do exactly what you wanted to avoid. You should try and think about what you really want, and what you are prepared to give up for it. There are chances your friend may be completely understanding and not have a problem with anything you decide, but you won't know that unless you have a conversation with him about it. Think about what you want, be honest with yourself as well as him, and be prepared for any reaction based upon what you think is best for your personal interests. Also be prepared for the possibility that this girl may not be who you think she is, because you don't really know her as well as you would like to, yet.

Should I tell my colleague I have a crush on her even if it means possibly losing my job?
That depends upon how much you want or need the job, and how you think she will react to your admission. It may make sense to meet her outside the office for coffee a few times before revealing how you feel.

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