There are some programming flaws. I never went to the gym to apply for a job, but later when I went there to work out, I could apply, and it talked about how I had applied before but got turned down. Angie I said take a hike to, but suddenly I'm working on a project with her, and given a choice of dominating her or pursuing a love route. I have no interest in punk looking, rude girls, and I already turned her down flatly. Questionable story choice: the mother acting like a bitch when you go to do the dishes at night seemed to come completely out of left field. Maybe there's a good reason for it, but she seemed to appreciate your help until that point. She never apologizes. I even get that that could just be her twisted style of humor, but there are no other indicators that she jokes like that. Also, you should be able to give it back, if she's going to dish it. Pardon the pun.
You aren't responsible for the well being of grown adults, who can take care of themselves, even if they're your family. Jeff seemed cool, and based on that, I would have cut my hair, put on a monkey suit, and applied, too. Have to be assertive and exude false confidence? Fine. That's actually typical for interviewing. Especially for sales jobs. Past that, though, the job seemed unquestionably unethical, so I wouldn't take it. Your mother would definitely be able to find another job that paid well, but it might be in another city. If your aunt lost her business, she's still a doctor, and they're highly in demand everywhere. I stopped playing after the crying event on the couch when the protagonist was determined to go back and work for Mr. B.
I'll give the office job a chance later, but I'm no longer invested in the character, or the game since I'm following a path I have no control over. If my opinion changes after giving the rest a chance, I'll post it.
I know I'm being a little hard on the game, and it's because I was pulled in by the story and characters, initially.