The Perfect Match by Ken Liu (from Brave New Worlds, 2nd edition)

From Brave New Worlds, 2nd edition,  

edited by John Joseph Adams

(Note:  This anthology originally appeared a few years ago but has been re-released with new stories as the first edition didn't get publicized well enough.)  

Sai relies on Tilly, an electronic aid that keeps track of his interests in order to help and recommend various products.  Jenny, his neighbor, sows seeds of doubt that allowing corporations access to his interests may be detrimental.  Sai starts to notice that with Tilly comes a lack of surprise and challenging thought.  Jenny has a plot to destroy Tilly.

(I can't help but wish I could own at least part of a Tilly.  This may function as a Valentine's story.)