Maybe she has or that's her way of kissing Max's ass... but she had at least one shitty relationship before and is kinda in the same situation as the MC.
About the gossiping part, girls love to gossip bro'. That shit is in their DNA ... don't avoid Annie just bcz she has a big mouth. You can always put some meat in her big mouth to stop the gossiping.
Morgan is a cool girl to hang out with, she kinda chubby tho. But I guess that's a matter of taste.
Osamabeenfappin waitress is married and has kids bruh ... after the fiasco with Kelly Jo I wouldn't bet on something with her. Maybe a quick revenge fuck if her hubby would somehow cheat on her but that depends on the dev. She don't look like the type who would fuck for a promotion or out of boredom like KJ does.
Most people hate on Fiona without even hearing her side of the story, so I guess we need some reinforcements cause we runnin' out of options.