Mary called me to ascertain whether John was dining at the club. Yes, both meanings are possible. In the case of (b), it would mean the (then) near future normally.
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pructusMary called me to ascertain whether Johnpructus! You haven't corrected that mistake yet!werewas dining at the club.
pructusCan this sentence also mean "Mary called me to ascertain whether John usually dined at the club", referring to habitual things, not one time thing?