Pat-
I agree with Michele--you can't predict what will happen down the road.
Another consideration, if it is your practice to discount multiple subjects on the same canvas, is that if they buy separate portraits you'll make more than if you put them both in one painting.
If he wants himself alone now, one way you might be able to influence them to follow through is to offer a discount on the second painting if they sign an agreement now to do both--one painting now and one later. For example, offer the second painting at 10% or 20% less than full price (at most). But don't discount the second painting by as much as you would if you painted both on the same canvas.
Offering it this way may help "lock in" the second painting, even if it is painted later.
Best--TE
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