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Is it reasonable to wait for someone to become important enough for a relationship but then be at too high risk of losing them in case of refusal?

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ThePerfectUsername · 70-79, M
No, that's not a very good idea for the simple reason that if yo take it to it's logical conclusion it means you have a five minute window in which to decide your life and if her buss happens to be running 15 minutes late you're fucked.

Far better I think would be for you to get to know multiple people simultaneously. Not with a view to "a relationship" as such but just to give yourself a better understanding of what sort of person makes you most happy and what sort of person you just don't want to handle.

Be honest with everyone you know... if one of them does something that endears them to you more than the others tell them. Let if grown gently step by step by step and see if it's mutual, and if it isn't just accept it and move one. The right person will be out there somewhere but you don't want to let it all hinge on that 5 minute window of opportunity that could all too easily be missed.