I figured out just how old Helen is supposed to be in the movie, thanks to two scenes in the movie and two (or three) deleted scenes from the DVD. Helen was 18 in 1974. That makes her 43 in 1999. And so are Janet and George since they all graduated together.
1. In the scene where she's driving George's Fire truck after the unofficial date, they talked about him taking her to the prom in a body cast.
2. George mentioned that he moved to New York in 1976, "the bicentenial trip." If you do the math, there are 23 years between 1976 and 1999. He couldn't have been too old, turns out 20.
3. In one deleted scene, or rather extended scene, where she gets the ticket from Dan after getting her "tires rotated," he mentions that that's her stop sign. Because in the summer of 1974 she had the accident that broke her collar bone and her nose was sideways on her face. That's why they put the stop sign in.
4. In another deleted scene, after Johnny's birthday party she and Johnny are having dinner and he asks her why she alway has to drive. She says when she was 18, her and her boyfriend Mark were going to a basketball game and he told this funny story about his dog eating his mother's panty hose and they were laughing so hard and he looked away or closed his eyes, and next thing she knew they were wrapped around a tree. It took a while for all the broken bits to mend. So she drives so she always knows she'll be safe.
5. Also another deleted scene Helen and Johnny talk about their first time, her's was 1975.
So if you put all the pieces together...
As for Lillian, she would have to be at least 20 years older than Helen. She mentioned to Helen about being with Constance, Miss Scattergoods, before she met her father. So there would have been some time there.
I think they chose Blythe Danner to be Lillian because she looks a lot like Kate Capshaw.
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