Easy to do as a single but not as easy with two. As long as enough time has elapsed after the first tee time the computer will let you book another round. For example you can schedule a round starting at 7:28 and the computer will let you book another round in the afternoon. I have done it numerous times with exec courses.
You might even try booking the early round and then wait until you get there and talk in person. There may be slots available after your round is supposed to end.
Good luck.
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