showing interest in people afraid of intimacy

Say you are friends with somebody because you meet them right after they got out of a horrible break up and are afraid to date anybody.

Do you think somebody can be turned off very easily and lose any desire you for if you express feelings for them and pursue them for a potential date if they 1. are emotionally fragile from a history of bad break ups. 2. have a history of pursuing the emotionally unavailable. Do you think it is easier to get friend zoned? What is the best course of action in your opinion?

do one of 3 things:
1. if you dont care about being friends, try and ask them on a date
2. do nothing. leave them alone and let them heal.
3. try the indirect approach - be there for them, make them feel better, show them a good time, etc (as friends) and see if anything happens from this (thats the route id go)

black all too late and I got stuck in the friend zone. told em I am NCing em till I am over it. I have just noticed red flags more easily now. If a woman has a fear of intimacy and a history of emotionally abused relationships, don't express anything that articulates feelings unless they express interest first.