I'm almost done with season 7, and I suddenly wished they'd done an AU episode like Felicity did in its final season, lol.
Like: who would Lorelai have been if she hadn't gotten pregnant at 16?
My speculations would be that her relationship with Christopher fizzled out after graduation from high school. Lorelai would have gone to Harvard and then gotten her MBA from Wharton.
Does this mean Rory would never be born?
Lorelai would definitely still rebel against her parents. Probably not go to an Ivy, but a state school just to be far away from them. Maybe even go international! Canada, or Europe... or if she really wants to be exotic, Asia! She would study Business or something artsy like Design (Fashion Design). Then meet a guy while she's abroad, and decide to travel the world after her college years for two years, work in charities and just have fun.
Then she's going to come back home, at about age 25 to start a business and she meets up with Chris and now she gets pregnant. She still doesn't want to marry Chris, but they move in together. She never goes to SH, maybe some other town. Rory is born 9 years later. (weird, that would be the exact same year I was born, 1993)