[X] Creep closer and eavesdrop. Issachar's been keeping too many secrets from you already. If you were supposed to expect company then he'd have mentioned it sooner, right? Maybe this way you'll finally get some answers.
[X] Wander off for a while and try to give him time to finish up with the woman visiting him. If it's important then he'll tell you about it without you having to force his hand somehow. Right?