I've heard people here talk about going on more than one date on the same weekday, but the logistics of it seem difficult to me. For those of you who've done it, how do you make it work?

My problem is that I recently had a girl sorta flake, but she asked to reschedule for tomorrow or Wednesday. Problem is, I already have dates scheduled for 7pm tomorrow, Wednesday, and Thursday too. Friday obviously isn't an ideal first date day, so my options are perhaps to try to cram her in early tomorrow or Tuesday (perhaps try to postpone my 7pm date until 8?). Otherwise I'm stuck working with a Saturday/Sunday afternoon brunch, which it seems most people advise against.

Trying to cram two dates into the 6-8 then 8-10 block seems tough if the venues aren't literally right next to each other. And does cutting the earlier date short look bad? What is the best way to manage having multiple dates on the same day?