Henry tells Rory that he tried to call Lane once, and Mrs Kim answered, frightening him so much that he never phoned again. This doesn’t quite tally with what Lane told Rory: that Henry rang once and got the answering machine, leaving a message that she listened to again and again before eventually breaking the machine. Perhaps Henry only counts the call where someone answered the phone (which Lane doesn’t know about since her mother took the call).
It is now nearly three months since Henry and Lane first met at Madeline’s party. That’s a long time for Henry to remain interested without doing anything, and he’s taken ages to talk to Rory about the situation. Perhaps he is as unused to dealings with the opposite sex as Lane – certainly they both seem to have made a bit of a mess of this situation.
Rory hasn’t been a real help either; she lives in the same town as Lane and goes to school with Henry, so couldn’t she at least have passed notes and letters between the two of them, or driven Lane into Hartford to see Henry? (Maybe even organised a Trigonometry tutoring class that Lane and Henry could have both joined!)
To be fair, Rory didn’t rely on Lane to fix her relationship problems with Dean, but Rory has a bit more experience with boys, much more freedom, and a generally far easier life than Lane.