So many people are still talking about how the thing keeping Jeff from being with Annie is the age difference, but where is that on the show now?
The age difference was definitely a point made in season 2 as being an issue for Jeff. But I don’t think that canon necessarily points to it being a problem for him now. We know from GI Jeff that he has issues with his own age (though I think the way he casually threw out “I’m 40″ when Elroy called him a young man indicates that he might not have as much trouble with that now). But there hasn’t really been anything in the past few season (outside of the ridiculous stuff from the darkest timeline during the gas leak season) that shows he has a problem with their age difference now.
And I think acting like that’s the problem is simplifying Jeff’s character. He’s always been someone who struggled with personal attachments. And while he’s made huge strides in that department when it comes to his friends, we still have yet to see him in a truly serious romantic relationship. Really loving your friends and family is one thing. Being in love with someone is another thing entirely, especially when it has the potential to mess with the friendship and family relationships he’s established.
We know that Jeff has a hard time letting people in, even when he loves them. We know that his inflated ego hides some serious issues with self-worth. He has a background that could make it tough to believe that a person making a commitment to him will definitely stay. He has a background that makes it tough to know whether or not he would stay. And from this most recent episode, we know that he’s continuing to struggle with that self-worth in regards to his friends moving on and growing beyond him, and he cited Annie specifically in that.
In short, there really hasn’t been any indication that it’s the age difference that’s holding Jeff back. On the other hand, we’ve been given a huge amount of evidence that his issues with self-worth and interpersonal relationships are the things holding him back.