Did I skip a couple chapters or did their feelings for each other come out of no where?? This was a bit jarring
Might have.
With
Taka-ara Takeout-kun, he's obviously been interested in her very early-on.
With Haru, the narration mentioned that she was rather lonely having few friends, none of which are interested in games like her.. so Taka-ara being a part of her daily after-work gaming life naturally had her grow attached to him. In Chapter 5, it's even to the point where she's jealous some guy is teaching him PVP skills instead of her.
Only until now has innocent attachment seemed to have fully-developed into romantic feelings, though she doesn't seem to be aware of it at this point.