It’s quite hard to create a Grand Theft Auto inspired video game without giving the player some romantic options and Sleeping Dogs does not disappoint and allows main character Wei Shen to date five women as he also performs his deep undercover mission inside the Triads.
The dates are found as the story progresses and gamers have to do missions linked to them in order to get to a romantic moment a little later on, but the interactions are pretty stunted and sometimes they lack any logic (I had a beautiful date in the park, that included pictures, but took place at night under a rain that probably also caused some floods).
This was with my first date and the rest of them might introduce different voice work and some other missions, but there’s no change of tone, which makes this entire section of the game somewhat disappointing, especially when compared to the role romance played in something like Grand Theft Auto IV.
The one exception is Tiffany, the Club Bam Bam hostess that the player can befriend after a session of intense karaoke (well implemented but nowhere near Yakuza levels).
If the gamer then chooses to move on to the hacker chick Tiffany demonstrated some agency and, after a number of missions, chooses to go out with another man herself, something which Wei Shen seems to take as a personal slight.
The dialog between the two is interesting and the main character accusing her of sleeping around (pun unintended) while he is clearly guilty of the same offense himself (although Sleeping Dogs never shows any actual consummation of the relationships).
It represents a quick glimpse of what the game might have done with the girlfriend mechanics as long as it spends a few more resources on this aspect of the game.