I can't help noticing that your experience is so close to Serena's. Maybe the two of you should share your experiences and when neither of your relationships don't pan out you can commiserate. It's the sad truth that odds are against things working out for you, especially in the long run.
After my disastrous marriage to an abusive fellow, and after a couple of years of inactivity as a witness, I met a nice 'worldly' guy who I saw on several occasions. Mostly, though, we spent hours on the telephone, planning our lives together. After much time on the phone, sprinkled between maybe one or two dates, he finally bore me down to the point where I consented to call him my boyfriend. Poor guy, we were 'boyfriend/girlfriend' in this manner for several years and I would never see the guy. In exchange for the promise of a relationship, he had to listen to all of my witnessing even though I couldn't tell him where the nearest Kingdom Hall was. You see, it is very difficult to walk away from the dogma. During our relationship, he kept trying to break off with me as our relationship was going nowhere and although it was painful, I would always agree it was for the best because in my heart and mind I knew it wasn't going to happen. Once I finished my schooling and went back to meetings I knew we would break off anyway. Of course, these 'breakups' were really intended to jar me into the reality of losing him yet it never worked and he would always come back sadder than ever because I could so easily let him go. This went on for several years. The guy was an atheist and after all of my bible discussions he finally came to the point where he began praying; first, with the hope that maybe God would get us together and finally, just for comfort from his sadness and loneliness. He turned to God, not the JW's though - they came to his door and were haughty and rude to him, much to my dismay. Finally, after 3 years, I came around and told him we could be together, a 'real' relationship. And after several days consideration, he told me, "nope, can't honestly imagine having a life without celebrating birthdays and holidays or any other of that JW mess." And with that he walked out of my life.
All of this is to say that when the indoctrination runs so deeply, it may not matter if the person is inactive, not baptized or crazy in love with you. In the back of a witness mind is the idea displeasing Jehovah, of a divided nuclear family life and/or the disdain of other witnesses and family who see you as having been weak for succumbing to a worldly person.