For ruby quest seems kinda broken : I can speak to her at job just as for sub...Ruby is the curly hair hottie working at the sport center reception on some days of the week.
You have to model in art class a few days to get the quest log updated to "meet (the black hottie whose name I don't remember right now, but she's with you in the art class) outside the college".
Once the hint says that, you exit the college and you meet her with a fancy sport car outside the college. She suggests you to do a photo shoot at a photographer studio in the beauty saloon. You need 80 charm to do so. You can take beauty services at the saloon to increase your charm.
About Fred: if you already found him 3 clients for his gym, and you set him up with a girl, you have nothing to say to him. That's a known bug of the quest log that never gets cleared in some cases.
Can pick her up for cinema but still this quest is broken...
For modeling i ve ever meet the black girl and done pics in the studio. this quest is also probably broken...