Kwint,
Well, if you are not concerned about facing disfellowshipment, etc. then perhaps it would be good to reply to any JW who approaches you, and giving them the benefit of the doubt.
State your position as you see fit, leave the door open to them to respond to you further from a sincere, human standpoint, and then wait to see if that's the basis on which he/she is approaching you or your immediate family members.
If they come to you as a JW in an attempt to get you to "repent and return to the fold", then you can politely but firmly reiterate your position. But at that point, they will have played their hand, and you will know where they are coming from.
The point is, it may well be that the person communicating with you may actually be "crying out for help", or wants to share his/her doubts with you. This is why it is best not to prejudge the situation.
There are a lot of things going on in JW land these days, and I happen to think that a lot of JW's are becoming "closet doubters" about a lot of things. You never know, but I for one am standing at the ready for anyone who wants to reach out. Then I will wait for them to reveal their motivations.
All the best with your decision.
Rod P.