Hi there @fearlessadz I've found these bug reports that sound like what you're describing. If you'd like to take a look at them, you can click Me Too on the first post on page 1 on each and add a reply if you'd like to do so, you should be prompted with a bug template to fill in with your platform and owned content. Each bug is tracked and fixed separately and it's helpful to have that information.
https://answers.ea.com/t5/Bug-Reports/OPEN-GTW-DO-CD-Business-employees-don-t-show/td-p/6419031
https://answers.ea.com/t5/Bug-Reports/OPEN-DO-Restaurant-Customers-Never-Order-Dessert/m-p/5469990
https://answers.ea.com/t5/Bug-Reports/OPEN-DO-Sims-won-t-stay-seated-and-eat-full-meal-at-restaurant-1/td-p/10208212
If there's more then here's the list of reported issues and Dine Out has it's own section in Game Packs.
https://answers.ea.com/t5/Bug-Reports/READ-FIRST-Compiled-list-of-reported-Issues/m-p/6374117#M223839
If there's anything you're not sure of just ask.