IT'S OVERTHINKING TIME! (My favorite kind of time!)
In terms of narrative structure, the only girls that make sense as final pairings are Haqua, Tenri, and (perhaps by retcon) Chihiro, since they are the only ones whose love for Keima developed without being the target of a conquest. It would be awfully hollow for the takeaway message of TWGOK to be that you can find "true" love by reducing IRL people to archetypes found in media and then roleplaying the perfect partner, actively avoiding being your authentic self.
With regard to compatibility, narrowed to those three, Chihiro likes him for no apparent reason; Haqua seems to like him mostly for his unexpected valor and the skills (perceptiveness, thoughtfulness, dedication) he demonstrates when he's "at work," to some degree in spite of his relentless gaming obsession; and Tenri, on the other hand, likes him for who he is at his core, including his relentless gaming obsession. This suggests Tenri is more compatible, though Haqua could help Keima "develop" more, if becoming more "normal" is even a good or desirable thing for Keima without us arbitrarily pushing our ideals on him. Part of what makes Keima an interesting character in the first place is his resistance to that very notion, so that leads me back to Tenri. Chihiro's compatibility hinges mostly on the notion that opposites attract, and that's pretty flimsy.
On an emotional level, though, the only girls he's showed an inkling of attraction to are Yui and Chihiro, and they are the only girls to really take the initiative with him. However, he thinks his attraction to Yui is merely a superficial aftereffect of her conquest, so we can dismiss that. And my opinion of his attraction to Chihiro is that it's more guilt (over breaking her heart) than love, something he hasn't had to feel in a real-world relationship before. She does challenge his core idea of what love and romance are more so than any other character, which gives a relationship between them some amount of narrative meaning. Ultimately, Keima's experience with dating sims leads him to view romance as a narrative device, fulfilling a functional purpose in character development primarily by healing that character's psychological wounds. This is a core principle of dating sims; that there is always a reason for love. Otherwise dating sims wouldn't feel like coherent stories but rather like a series of coincidences. If TWGOK wants to poke fun at the core elements of such games, then Chihiro is where TWGOK goes from poking to jabbing, because her affection is without proximate cause and no longer serves a narrative purpose after her Loose Soul arc. She's already put herself on a self-sustaining path to character growth, so there's no narrative reason for her to want to love or be loved. But that's how she feels, period, end of story. That is just completely incompatible with Keima's worldview, and arguably more realistic. And so she might force Keima to grow as a person in order to reconcile that, unless of course he were to chalk it up to the real world being a confusing mess not worthy of respect, which would be authentic to his character as noted earlier.
Ultimately, Chihiro does end up making the most sense, followed by Tenri and then Haqua. I don't really like that conclusion because I didn't like Chihiro in the manga, but, for what it's worth, she seemed to turn out more likable in the anime. Also, the author seemed very committed to making sure she fulfilled the best narrative role on every front. This is ironic, because one of Chihiro's narrative roles is to provide a counterpoint to the idea that having a narrative role is important. If we really took that message to heart, the best pairing would be Keima x Miyako or another side character, someone who's as far off the radar as possible without simply not being a part of the story.
But Shiori is clearly best girl, followed by Kanon and Haqua. So there. |