I'm pretty sure season one was filmed in 2017 (featuring Mardi Gras 2017).
I feel bad for Jeff because I think his demons are real and his reactions are authentic. Even acknowledging that he pushed Reagan away, it must still hurt him to realize how much his demons are sabotaging his ability to be happy and seeing how Reagan moved on so quickly in every way possible, it must have brought on a lot of self-doubts. Said it from last season that Jeff needs a lot of help and I think his friends are patient with him because they know that his behaviour is fuelled by other issues but that's also not a reason to take advantage of their goodwill toward you. At some point, you have to be willing to help yourself rather than expect everyone around you to simply accept you and your demons as you are.
Doug was horrible with his timing and I agree with Barry that the pregnancy news should have come from Reagan, however, we saw Reagan say that decided that she wasn't going to tell Jeff and I wonder if Doug was aware of that. If he was, then I can understand why he didn't want to be in Jeff's home, smiling to his face and holding back such a secret...but they're friends, surely he had his number and could have had that conversation at least earlier in the day or later that night once the dinner was over. Watching Tamika rub salt in the wound not believing that Jeff didn't know, I felt like she was making a point. If Jeff and Reagan are so close like they claim, why wouldn't Jeff have known about her pregnancy? He was the first to know about Reese and he was the first to know about the engagement. I think Tamika was pushing the issue to demonstrate that the whole friendship that Jeff and Reagan are peddling is a facade.
I'm actually liking Jon Moody this season. He's funnier than I remember from last season. I loved the bit about Justin being on Moody Duty, haha.
If this show is producer driven in any way, I honestly don't see it as being obvious. So maybe it's possible that Kelsey is being intentionally extra about Justin but a part of me doesn't think so.