Yes, I know he didn't have feelings* for Heartless Woman. Yes, I know he thought that feigning a match with Heartless Woman (by cutting off his emotional side) would be easier than feigning a match with another girl (by cultivating a not-yet-existing affection). Yes, I have seen the movie and I know where his decision eventually led to.
The question though remains why he chose the "easy" option over the more challenging option. You're dodging that question by ignoring/re-interpreting/mis-appropriating my "math/amputation"-example. Your first post tried to make it seem as if "David said that X is harder than Y" is the clear and conclusive end-all-be-all explanation to the OP's question.
[*] David indeed stated that it would be easier to pretend to not have feelings that you do have, rather than to pretend to have feelings you don't have. Judging from other threads on this board, it seemed that some viewers interpreted that statement as David having feelings for Heartless Woman but choosing to pretend to not have feelings for her in order to secure a match with her (which, according to his statement, would be easier than feigning to have feelings for a woman he didn't have feelings for at all). I thought you might be one of those viewers, hence why I felt the need to emphasize that his statement doesn't necessarily imply that he had feelings for her.
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Keiko Matsui & Carl Anderson - "A Drop of Water"
http://youtu.be/kPUENUUuqSk
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