I've been thinking about this a lot. I think a lot of people are like me (especially after researching the witnesses via sources like this board), in that they attempt to convince their family, weather directly or indirectly, that the WTS is wrong. While there is a possibility of this working, the chances seem small, at least for dyed in the wool witness families. I've tested this out a bit with my family, and it didn't seem to work too well with them, not to mention cause me a lot of stress and frustration. There is another approach I've been thinking of. Ironically, I haven't used it before because I was trying to be 'straight up', more honorable than the witnesses' methods of convincing people. But I may be looking at this whole situation not quite right.
Anyway, my idea is to just avoid the whole topic of the WTS, and try to get as close to them as possible. And try to have as much fun as possible. Maybe even go to some gettogethers or something. The main pursuits are to be close to them, and to build my own fun life. The goal, however, is to win them back form the WTS.
The reason I started to think about this approach is that I was reflecting on my own feelings growing up a witness. Direct pressure didn't work on me. But it used to really confuse me to see witnesses or people associated with them (ie unbelieving family) carrying on as normal and having a great time - not pioneering, building a career, going to university, dating around, buying expensive stuff, hanging out with unbelieving relatives and having fun.
I'm not articulating this very well. But has anyone done this?