forget about trying to get him to be your boyfreind for now, try to encourage him to stay in school and finish.
college drop outs are worse than high school drop outs, in that you might always feel like a failure.
whos throwing that money away?
maybe if you can get him to stay in school and get his degree, and in the mean time once in a while, present some small issues or bible questions, so that he may start to ponder about the religion. let him learn how deceiving it is.
them maybe just maybe when school is all done, he will be mature enough to let go of the guilt of leaving such a controlling religion. watchtower examiner on you tube does a fantastic job of making a jw think.
by the way, I was told years ago by an elder that you cant get disfellowshiped for marrying a worldly person, you get disfellowshiped for committing fornication beforehand. It depends on how the elders interpret the bible. but no place does the bible say we have to marry a fellow jw. it says marry in the lord, which to me means that when you marry, if you have the lord in your life, no matter what faith you claim to be, you have his blessing, as long as the marriage bed is not 'defiled'.
but then I think those rules were only for those under the law. who knows.