There are no guarantees in this life that dating a former jw who is awake or not awake-or dating a never been a jw is going to work out. In the congregation I used to go to, there were people who were married to unbelievers for fifty years and seem to be happy, then there were jws who married jws and were divorced within a few years. And there were jws who had been married to jws for fifty years also and were happy. Then I was reading not to long ago that Goldie Hawn and Kurt Russell have never married but have lived together for over 35 years.
More than anything, I think it has to do with a person finally getting to a point where they learn how to love and treat another person. If both of them are there at that point, it will work no matter what the other person believes. That's just life.