There's a difference between a person who grew up watching video cassettes on their neighbor's VCR, and a person who (barely) watched recaps over 1MB/s DSL. Two completely different childhoods, two completely different cultural experiences, less than 15 years of age difference, both people have had "a couple years out of school and a couple years of being able to drink."
It's not unworkable, but it's quite like a relationship with somebody from a far-away foreign country, maybe without the language barrier.