Conversational Hypnosis help for a Newb

So here is the spot I find myself in and i could use some help...

I am a surgeon and very interested in the process of learning and memory. I am also very intrigued by reports about hypnosis for surgical pain prevention or treatment. I have just finished conversational hypnosis home course and struggling with my first two "clients".

I have two people I want to help or maybe 3 (If I include myself..just need to do the self help to let it go).

Briefly one is my son who has aspergers and is very bright but content to watch TV and Stock shelves at walmart. He says he wants to do more but challenges with writing at school keep him from pursuing school beyond his current associates degree. Just not sure where to start because he has such a flat affect (autism spectrum) and almost no eye contact. Any special thoughts about where to start to get him to trance and embedded suggestions for a more productive life? Is hypnosis in aspergers advanced level or easier or is it all the same in terms of difficulty?

Second is more pressing/urgent. My former scrub tech is child of broken home and is at end of second divorce and in hot pursuit for another husband. She has 3 kids and 3 different dads for those 3 kids and pursuing a guy who is just a variant of the ones she has had before. She is always talking about being there for her kids and in the past comments about how she did not want to be like her mom with multiple husbands and BF’s. I think that fear of being alone or stigma of being not wanted or loved is driving this… not sure how feelings toward dad relate here. She has told me very little about him and her relation to him.

She trusts me very much and tells me I understand her better than anyone else and sometimes better than she understands herself.
I have listened to the whole conversational Hypnosis home course and intellectually I get it ( attention, bypass the guardian, state, Nested loops and Embedded suggestions and confusing language, pacing leading, and revivification/fractionation). I also think i may be over thinking it and trying to cram too many techniques in and then it will not be conversational. I want to start simple and relax but need to know it is working. I have not had a lot of time to practice these as my surgical practice does not allow it.

Main issue is I am note sure what the “states” are that I am looking for. State of not feeling alone? And how to get her to past just talking on the phone so I can use some triggers/anchors, and what stories to tell…. A walk in the woods and a talking rabbit would not be covert!! She is used to me telling stories about work just not sure what the “line/state” in the story needs to be to get her to walk back her pursuit of another guy. I know I need to get her to open up a little more… “What do you really want? “ so I can find her personal trance words and get the feed back loop going, just not sure how to get started and feeling the pressure of time constraints.
Is talking about prior bad experience a bad idea? ie you are getting yourself into the same bad thing you have done before... since her conscious mind does not agree that she is doing the wrong thing?

I would greatly appreciate some direction.
thanks for your thoughts.