A Brief Note about Jeff's character development
So, when rewatching S1, it's fairly obvious that Jeff is totally reliant on speeches and "using words to get things" to the point that he's characterised as eloquent, witty, and manipulative.
However, as the seasons/years go on, this trait of Jeff's gradually becomes less prominent and by Season 5, there are two instances where his gift of gab fails him because his grown beyond using tonnes of unneccessary words to make his point anymore.
These two instances are Basic Intergluteal Numismatics and Cooperative Polygraphy. In the former, Jeff tries to make a speech to comfort Annie as they begin grieving the loss of Pierce, but it's obvious that he struggles to make sense of what's happening and I'm pretty sure he scolded himself later for how lame his words to Annie were when he was trying to comfort her and only made an awkward statement about how life is a container for weird stuff before hugging her, but maybe that private hug alone with her was more what she needed in that moment and Jeff instinctively knew it, deliberately fumbling his speech.
The second instance is at the end of Cooperative Polygraphy, after Troy's stated his intentions to fulfill Pierce's obligations and travel around the world. Annie (Greendale "Mom" like) urges Jeff to say something and convince Troy not to do it, but Jeff can only say that he's speechless.
This lessening of Jeff's reliance on his speeches makes me believe that he's faithfully written in the diary that Annie urged him to get two/three years ago, which explains how he's at this point by S5. He doesn't need to be reliant on his speeches and his words anymore, he's learnt to measure out his words carefully and to chose them meaningfully, because the people he's speaking to matter to him and he wants to give them the fullest consideration - and for Jeff, that shows in S5 in how he speaks to the people he cares about.
And this isn't to say that Jeff's habit of making speeches isn't totally gone - he makes several speeches during the early eps of S5, but midway through it, they begin to taper off. That has been my observation.
However, as the seasons/years go on, this trait of Jeff's gradually becomes less prominent and by Season 5, there are two instances where his gift of gab fails him because his grown beyond using tonnes of unneccessary words to make his point anymore.
These two instances are Basic Intergluteal Numismatics and Cooperative Polygraphy. In the former, Jeff tries to make a speech to comfort Annie as they begin grieving the loss of Pierce, but it's obvious that he struggles to make sense of what's happening and I'm pretty sure he scolded himself later for how lame his words to Annie were when he was trying to comfort her and only made an awkward statement about how life is a container for weird stuff before hugging her, but maybe that private hug alone with her was more what she needed in that moment and Jeff instinctively knew it, deliberately fumbling his speech.
The second instance is at the end of Cooperative Polygraphy, after Troy's stated his intentions to fulfill Pierce's obligations and travel around the world. Annie (Greendale "Mom" like) urges Jeff to say something and convince Troy not to do it, but Jeff can only say that he's speechless.
This lessening of Jeff's reliance on his speeches makes me believe that he's faithfully written in the diary that Annie urged him to get two/three years ago, which explains how he's at this point by S5. He doesn't need to be reliant on his speeches and his words anymore, he's learnt to measure out his words carefully and to chose them meaningfully, because the people he's speaking to matter to him and he wants to give them the fullest consideration - and for Jeff, that shows in S5 in how he speaks to the people he cares about.
And this isn't to say that Jeff's habit of making speeches isn't totally gone - he makes several speeches during the early eps of S5, but midway through it, they begin to taper off. That has been my observation.