Should I go on a date with him?

Illustration/Uday Mohite

A friend of mine recently told me he has had a crush on me for many years. I didn't react, and said I was flattered, but I have been thinking about him since we had that conversation. He and I have been friends for almost a decade and know each other's families well, too. We have also both been single for a while and are familiar with our exes and past relationships. I am beginning to think that I should go on a date with him a few times if only to see if my feelings towards him change and turn into something else. Is this a bad idea? I can just let things stay the way they are and I know he won't be upset, but part of me feels as if I should try it because if it works, it may be life-changing for us both. What should I do?
You should go out a few times and see how you feel, because it seems as if you have weighed the pros and cons of this already. If he seems mature enough to not have a problem with you rejecting him, that is a great thing because it implies the two of you have strong lines of communication open. You're right about the possibility of this being good for you both too, and you can always discuss the possibility of nothing happening to avoid any unnecessary awkwardness in the future. Go out, see how you both feel, and keep talking about it until you both have a better understanding of what this means and what your expectations from each other are.

I want to tell my girlfriend to go easy on her work because it eats into our personal lives, but she believes I should keep her professional life separate. Is she right or am I being too pushy?
The only answer that works is one you arrive at together, because the two of you alone can decide upon boundaries involving your personal and professional lives.

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