+100 but I assume it's just showmanship for his frum audiences
I honestly don't know who is being discussed here. I was just making a statement based on observation and reading.
I buy for my DW the Israeli Mishpacha and Sha'a Tova magazines every week. While I don't find much value in them, the exception to that is the weekly column in the Sha'a Tova magazine of Rabbi Asher Yechiel Kasel who runs an educational facility for teenagers that went (or are in the process of going) OTD. I find that there's a lot to be learned from his writings (and obviously from his experience). I am unaware of any book that he wrote, nor of anything in English from him. I did find the following link to some of his articles, which I highly recommend:
http://www.yahadoot.net/category.asp?cid=27I think we will all do better for ourselves, our children, and our communities, if we would approach everyone (including ourselves) as someone who we would like to be mekarev out of pure אהבת ישראל. We will all benefit from a much richer Yiddishkeit experience, and much better interpersonal relationships.
Obviously the case in question under the current discussion is very different, as it involves a more mature (as far as the calendar is concerned) individual who already has a family of his own. I am no expert by any stretch of the imagination, but some of the advice given above of just listening to the individual in question sounds right to me. It would obviously be best to be guided by an expert (and a LOR who specializes in the fifth part of Shuchan Oruch).