Interesting! You made me take a closer look at the old instructions. In the instructions, it says that reservation shops completed with a guest are eligible for additional reimbursement to cover guest's W&W burger and paired glass of wine. Max reimbursement for two - $125.
My guest and I went over the $75 reimbursement, but I checked just now. I was reimbursed for the full meal!
Under these conditions, I personally think you would be ok dining with a guest, but asking for separate checks. To make full use of the reimbursement though, you're allowed to order additional items.