Should I date my close friend?

Illustration/Uday Mohite

I have a close friend who wants to be in a relationship with me. We have known each other for years and like each other a lot, but I have never had romantic feelings for him. Since he told me how he felt, I have begun to look at him differently and I can see why a relationship may be possible. My worry is how things may change between us if this doesn't meet our expectations. He knows a lot about me, obviously, and I know him too, but there are aspects of our personalities that may only show up when we change this from a friendship to something else. Is this a huge risk? Should I just tell him that it's not worth losing what we have?
Being friends with someone is always great when it comes to changing the nature of your relationship because it gives you immediate advantages. There's a sense of familiarity, coupled with trust, which obviously makes things more comfortable. Having said that, the risks you ask about are the same no matter who you choose to get into a relationship with. This requires work from you both, and there is no manual that can help. There is no guarantee that a romantic relationship with a friend may work out any better than a relationship with someone you don't know as well. You won't know what your expectations are either, unless you talk about them, so that's a great place to start.

My girlfriend says I am not emotionally available, which is true, but she doesn't see my reasons for this. I am constantly under a lot of stress, and she doesn't get that. I want to try and be more understanding, but I don't know why she doesn't see things from my perspective. How do I get her to be more flexible?
You can try doing a better job of explaining what you are stressed about and how it's affecting your life. You accept her argument, so why not try harder?

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