I'm on PS4 (5 actually) and have had this constantly happen.
My Sim was asked on date. Arrived and he left. Right away called and asked him on a date and he arrived and the date happened no problem. He did have a job, but not sure why the one scenario worked but the other didn't. He initially asked me.
Fast forward, they had married and now have teenage kids. The one was asked on a date by his girlfriend. He showed and she left. He turned around and immediately initiated a date with her and she never showed. I tried several times and she never showed. She does not have a job. Then one of the daughters was asked by her boyfriend and when she showed he left. I tried the the same with her; having her call and ask him on a date. He never showed. I know he also did not have a job. I didn't bother to keep trying on that one since it didn't work with her brother.
I haven't had the vendor issues. I haven't gone to many of the festivals/events. I'm so goal oriented I've been getting all the children's skills up to prepare for college.
