Based on all the different majors she took it seemed as if she is very intelligent and was a good student but not very focused on reaching the goal of graduating due to her inability to stick to her decisions (except of course when it comes to her surgeries but I don't think she was thinking about that in college..not yet). Also looking at her relationship with Toby's Mother which started in college as Bree's "experimental lesbian phase" ..it was probably then that she started to look into her Transgender identity and Bree became focused on that instead of graduating college. Even her mom tells her at dinner that she could never make up her mind..not even with choosing a degree. It is very easy to just leave college unless the student is focused on their major and graduating. As other posters mentioned, that little piece of paper is worth a whole heck of a lot if you want to get a good job or follow up towards a good career.
Bree probably felt that pursuing her Transgender self was more worth her time than getting a degree. I think it started to snowball for her. Her family probably would give Bree the money she needed if they knew she was in college (& college is expensive).They wouldn't know if she was changing her appearance if she was "away" at college. She could have gotten a lot of those less drastic surgery while she was in college for ten years. Her family has a lot of money..her Mom offers her $200.00 and more from the house safe when Bree tells them after dinner that she needs 1,000$ even though the mother doesn't approve of Bree's lifestyle. Also, when Toby hit Bree it was Bree that her mother ran to and cradled while Toby made off with her purse and the sculpture. Despite her mother not approving of Bree's "lifestyle" it seems that she does care and would help Bree if she asked for the money. Later, when Toby asks her why Bree doesn't live at home (with her parents) she says her parents come with the house. I can see Bree doing her best to not depend on them anymore..it's too many negative family drama and she doesn't need that. She has a stable life without the her parents in the scene needs to start her own life as a Transgendered person and nothing is going to get in the way of her getting her surgery. Maybe she had better jobs in the past and she saved? In any case, she doesn't seem to be in debt. Getting a diploma after ten years of college is quite expensive and no one is asking where she got the money or why her low paying jobs do not screw up her financial history (student loans and all that stuff).
Regarding the jobs themselves, at the Mexican restaurant, I think Bree actually likes working there because the other employees "get her". She is different than them, she is afraid of being called a freak...that she might be a freak but at the restaurant everything seems low key, they like Bree for who she is and she probably won't be recognized or hasn't been recognized as Transgendered. In the last scene of her working in the restaurant she actually looks happy & smiling (although that could be because she had the surgery). Also her telemarketer job gives her her own space and no one can see her and call her a freak.
Oh and one other thing: Bree tells Toby that she'd like to become a teacher. Once Bree is whole & totally confident as a Transgendered person, surgery and all, she could always go back to school to get her teaching degree. Of course, she had just met Toby and almost everything that came out of her mouth was a lie. Maybe the teaching thing was a lie but maybe not. It's very rarely too late to go back to school & get a degree.
It doesn't matter how many degrees you have. If you are miserable as a CEO or a Film Director or as intelligent and rich as Howard Hughes what's the point in doing that job? Howard Hughes was insane. Bree is not. Ever work as the producer of a film, commercial or video? in a big famous Hollywood position? Tom Cruise's role as Mega Hollywood producer, Les Grossman, in Tropic Thunder, isn't far off the mark. Crazy. Stressed. Anger...Rage... Sometimes it's all about your comfort zone and what you can realistically do (as in making enough to pay your bills & be fine with that).
Bree genuinely seems to like her life and herself and accepts it more and more each day. Who cares why she is in a low paying job without a degree? As long as she can pay her bills and is happy? She seems to be okay with the way things worked out. And that's what really matters.
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