Helen: It sounds like a boy Garry's age needs a man around the house.
Tod: Well, it depends on the man. I had a man around. He used to wake me up every morning by flicking lit cigarettes at my head. He'd say, "Hey, asshole, get up and make me breakfast." You know, Mrs. Buckman, you need a license to buy a dog, or drive a car. Hell, you need a license to catch a fish! But they'll let any butt-reaming asshole be a father.
Julie: I can't do this! This is too intense.
Helen: This is marriage.
Garry: What is it with all the women in this family, that makes all the men in this family wanna leave?
Gil: We'll throw away the TV. We'll perform Shakespeare in front of him.
Nathan: Did he say "Cool"?
Gil: Cool.
Gil: Keep Patty away from Larry - suck the intelligence right out of her.
Karen: He likes to butt things... with his head.
Nathan: How proud you must be.
Justin: Who's that?
Gil: It's my kid brother, Larry, your uncle. Don't give him any money.
Justin: I won't.
Marilyn Buckman: Cool is adorable. Adorable! Why didn't you write us when you had a son?
Larry Buckman: I didn't know myself until a couple of months ago. You see, a few years ago, I was living in Vegas with this girl. Showgirl. She was in that show 'Elvis On Ice'. Anyhow, we drifted apart, as people do in these complicated times, and then a couple of months ago, she shows up with Cool and tells me "You watch him. I shot someone. I have to leave the country " That's a parent?
Answer: The movie is being told in a linear timeline. You have just about all the information right! I think the one thing you are letting throw you off is your assessment of the Super Bowl. You are surmising that they had just watched the game that day, but my assessment is that they are talking about the game from months ago (bearing in mind that Larry has not been around for years and has not seen his father since the last Super Bowl). My belief is the movie takes place in May. That would add up with Kevin's next year of school being 4 months away as schools usually start in September, and the math also works out with Karen's February due date. This would also explain your concern about the weather. As for Helen's baby, it is not made clear whether or not she married Mr. Bowman, nor does it really matter for timeline purposes, but they consummated the relationship not long after the first date and she got pregnant.
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