I think it's perfectly reasonable to try to befriend someone before asking them out. You may find that as you get to know her that you aren't as interested as you thought. I think you can strong and stand up to your T and say "I know we disagree on this, but this is how I want to handle it." Your T should respect that you can only do what you are comfortable doing.


UNLESS...Are you female and interested in this woman as another female? Because then I could see how it's a little weird to be befriending someone you are romantically interested in versus just asking them out. Doesn't really change my thought on the matter, but I can see how it maybe could be a little weird or even seem creepy to befriend someone in this way.


But honestly, people do this every day in every friendship, regardless of whether we are romantically interested. We feel other people out to see if there's a connection. Seems odd that your T wouldn't see that.


Seesaw