Great, thank you for your help! I still don't have a ton of money in the game yet (like $4,000) but it seems to be adding up faster. I'll try a new outfit out before my next project and see if it works. :)
I've tried wearing clothes with stars when working on a project, but the extra star wasn't given to me. Do you think that every item being worn has to be one of the star clothes (same goes for the hearts and dates)?
Also, I tried to go on a few dates, but most of the dates made comments like "I wish you prepared for our date" or "I wish you dressed better" (something along those lines). I'm not sure what are considered "quality" clothes for them?
I was having this problem earlier and I finally fixed it. I had another task available (something like doing an ad campaign when Simon called me with the different job options) so I had to go and complete that first and then Simon finally called and I was able to move on to the main goal.
Thanks for the help everyone! I may end up going ahead and adopting the cat. I also noticed that you can add a pet to your home when buying furniture. I bought the $2000 Hollywood home and there's an option to buy a dog for 20 stars. It might be like this in all the homes but I'm not sure.