Re: Am i coaching badly? (AK hand)
I would call the flop as your student did. This is not a passive player based on an AF of 1 combined with very loose play.
Case 1: He has a pair (likely IMO). He knows what cards you are looking for and is likely to pull the stop-n-go when you miss the turn.
Case 2: He is semibluffing. When he misses the turn your free card play backfires and you lose money. It was better to go for one bet on each street. When he makes his flush or straight he will probably bet out because he's seen the free card nonsense much too often to try for the checkraise. Once again your flop raise has lost you money.
Having raised the flop you need to take the free card. Aside from the reasons already given there is the consideration that a third diamond may river. Now your turn check allows you to save some money by folding.
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