I think it only seems that way cause the extra chapters don't follow the same chronological order. It's only been ~10 main line chapters since they openly started hanging out. Another 10 chapters before that he was still struggling to speak to her normally.
I've been seeing TLR references quite a bit lately. It's kinda impressive just how popular that series managed to be just by putting cute girls into lewd situations.
"Long sleeves and pants"
How are we not past this point with this dude. It's been 200+ chapters, I'm not usually one to yell about lack of progress or whatever but come on.
Every time I read another chapter of this I ask myself, 'why am I still reading this?'
And I never have an answer.
I'm convinced that she's actually a massive perv and is just using all of the "protect my virginity" stuff to justify it to herself.