You seem to be a great friend to have.
I agree 100% with joannadandy.
The WT uses guilt, study preparation,service and meetings and the"you're not doing enough" refrain to keep their members well-occupied. Wonder why many can't keep up and feel depressed? The WT maintains their members inside the WT circle by calling outsiders, even relatives, "worldy" and forbides any 'fun' association with outsiders by labeling holidays as pagan. Week-ends are okay if they are spent in service and at meetings. I've noticed some who do well and finally wake-up and leave are those who get really involved in outside interests but this can be easier said than done. Perhaps you can get your friend interested in some non-JW activities without her feeling she's neglecting her religion or that you're encouraging her away from her religion.
Most witnesses don't bother with education and aren't bothered by the WT viewpoint on education because the "end" is so near. You might try the approach that the "end" could still be some years away. This can be argued by the latest WT prediction 1975...27 years ago ... and yes I'm 49, been there, done that, never got a decent education, and am now doing cleaning (the WT's preferred career choice) with absolutely no benefits and in 15 years its pension time ohh-ohh. But then I'm the stupid one. You could perhaps mention that you believe it would be a good idea for the young man to further his education to better provide for himself and his future family. I've been humming this 'just in case the end comes later' tune for some time now and have found a few listening ears.
good luck!!!!!