Corrected entry: There's never any real explanation of why Bridget's father wants to keep her away from Jake. Bridget has already had the baby, so now she's going through parenthood alone, with very little money, and unable to go to a good school. If she were with Jake, or perhaps married to him, he could help support her financially, and she could even be entitled to his pension as a war hero.
Corrected entry: Early in the episode, Tru says that one benefit of reliving days is that it can help her avoid wearing bad outfits. How, exactly? If she put it on in the first place, then she must have thought it looked good. Unless she expects someone to tell her anytime an outfit of hers is unattractive, reliving the day won't help.
Correction: Sometimes a woman puts an outfit on thinking it looks good. However, when they go out in public and by chance walk in front of a mirror or reflective window or even just looking down at yourself, you can start to not like the outfit anymore and wish you could change. (Personal experience here).
Correction: The father hates Jake and only connects him to any negative effect the baby caused. It's not very reasonable, but being unreasonable is a part of his character.