I heard that one is supposedly easier to get than the one where you get her to cut back on her smoking but I got that one my second playthrough. The 100+ cigs I still haven't done.
Cutting back on the smoking I did while trying to get the conked on the noggin once with a Sax achievement. Really needs you to know what you're doing but made it with 16 cigs. 100+ can be easily done through a minor exploit and her having cigs and a lighter on hand. And you can easily get 8-9 alone from your final segment with C.
Gotta start up the third sometime, still a really solid series.