I grew up in an expat community in Sumatra, and everything we had to get was in Singapore. I'm not sure how many times I flew from Singapore to Pekan Baru, but I did it once a month for three years, and at least 50 times in the other years. I figure I've flown that route 100 times (round trips).
We also flew to San Francisco and back once a year for seven years. I think I've flown the old SQ001/SQ002 route about 5 times. I'm not sure how many times I flew between HNL and SFO, but I've been to Honolulu about 20 times. All except one I either flew either from, or to, SFO.
Unfortunately, now a days I don't have any regular flights (you have to fly regularly to have one) I have flown between OAK-PDX four times in the last three years, but didn't do it this year. I live in the Bay Area, so obviously I've had a lot of flights between OAK-LAX. I try to avoid those flights, because LA is the scourge of the earth (my Northern California bias, I'm not allowed to say anything good about LA).