[Vena]

Originally Posted by relentlessflame

Vena: good observations all around.

Well, I think he had a few trump cards that helped. First, that initial encounter in the park that clued him in that Airi wasn't a bad person. Second, Airi's continued friendship with Sakuno, and Sakuno's reassurances. Third, some minor past successes where Airi momentarily showed her true self. And finally, Airi's own arguments, which he effectively used against her, leaving her with nowhere to run.

I think he wasn't just trying to diffuse tension in general, but specifically with Airi, with whom he took a particular interest (due both to that initial encounter, and her role in the class). At the end of the day, they were forced together and would have to keep working with each other anyway, so he wanted to diffuse the tension with her as much as anything else.

Of course, your observation about the potentially two-faced way we could take Shingo's actions is clear for another reason that is more evident when we consider the source:

Spoiler for comparison to the game, to this point only -- no future spoilers... but do not read if you want zero source insight:

Everything we've seen so far happens whether you're on Airi's route or not -- it's the "common route". At this point, Shingo has a friendship that could rather easily be turned into more, but there are other possible routes that Shingo can follow. So the anime is playing it coy here, not wanting to absolutely confirm what route we're on. Incidentally, all of the decision points up to this point in the game have also been deftly avoided (such as in the grocery store, and when Miu asked Shingo to join the club). They are deliberately trying to ensure game players don't know what route they're following, though logic based on simple observation does lead to certain conclusions...

The one thing that does need to be noted, though, is that he could have just as easily blown the situation far out of proportions with Airi had the grocery event not occurred. He did have prior glimpse into her character to some degree (though how much weight he can put to it with just one such meeting is questionable) and her continuing friendship with his sister is a hint he also had going for him, but to put himself into a possibly negative position by requesting a study session sure is a perplexing thought for someone who supposedly avoids bad atmospheres. Had everything not played out so well for him with the grocery store, he'd have been in a situation that either:

a.) Exploded.
b.) Ended in bed.
(Also nothing could have happened but that's boring, so ignore that possibility!)

Now, I would have found the latter pretty hilarious and quite the change of pace for a story of this genre but I doubt such a dynamic would ever be taken up in a non-Nice Boat-ending. He really didn't need to put himself into such a possibly awkward position by making his request for study-time because, as you said, they'd be stuck together every day anyway and he'd have had plenty of alone time with her in a more proper environment to solve the problem.

At this point, I don't even think this analysis has much to do with the show or whatever may come of it, and just a delve into the psyche of the writer. :P

As for the rest:

Spoiler for oh no!:

I have never played the game but I can understand the idea behind the approach by Manglobe. It keeps everyone on their toes, the only problem is that if they wait too long you can make the end seem very far out of left field or awkward because you missed many opportunities to address the other possible heroines and they don't have the same time as a video game to make things happen. So in a way, by missing flags, they may also be closing paths.

Originally Posted by relentlessflame

Those were my feelings as well. Based on what they've shown in the anime, and the emphasis they put on Shingo's reactions to certain characters, that certainly seems to be what they're hinting. But as you say, the next few episodes should provide more hints about the "turn", if there will be one.

Bring on more cute Airi!