You'll want to check out the menus at someplace like allears.net and see which one works out better. However, since a gift card is basically the same as cash, won't it be the same whether you pay with GC or OOP?
It should be.
For the OP, if you're not on a dining plan, use the GC at whichever restaurant you go to first.
Assuming a $75 meal at Y&Y and a $150 meal at TRex (note, numbers are made up, hugely inflated, and all that stuff), the total would be $225 for both.
If you used the GC at Y&Y, you'd then have a $25 meal and a $150 meal, totaling $175. If you used the GC at TRex, you'd have a $75 meal and a $100 meal, totaling $175.
However, assuming the order is Y&Y then TRex, if Y&Y is $35 and TRex is $45... If you use the GC at Y&Y then the remainder at TRex, it'll end up being $0 and $30 totaling $30. If you skip it at Y&Y then use it at TRex, it'll end up being $35 and $0, totaling $35.