my brother has 2 felonies and just ended a LTR and is starting to date when should he come clean about his past to his dates, girl fiends ?

He has been out for almost 2 years now and never had any major issues before except he said a poss. for pot in the late 80's and a trespassing in college about the same time both misdemeanors but who cares thats 25 tears ago . He was sentenced to a year for each felonie with half time so he did a year. He got out in 2012 and completed parole and has been dodne now for a year but he had to register as a narcotics offender for 5 years so he still 3 to go.he is working on getting his record expunged but ithey said not until % years from the date of completing parole.He is also having a hell of a time finding work inn his field with these items popping up everytime they do a background search and he says he is very upfront when he interviews so he thinks he should take the same approach with dating I told him to at least wait to see if there even something there, so at least he would have the chance to make a good impression on them first.. We can't see eye 2 eye, on this issue.

what are your thoughts?