Damn, that's a nice love letter. Straight to the point and absolutely honest, while seemingly promising little useless stuff getting in the way of the fun.
I mean, unless there are topics he's not comfortable of answering, I don't see much reason why he couldn't. Last chapter's virgin topic could have been played better, but he made the right move directing her to the nurse in regards to sex, though that kind of topic should be asked to the parents, personally, especially these days when schools have become less trustworthy for these things.
from my understanding, the entire point of this manga is that he is that he finds the questions she asks him as ones he's uncomfortable to answer.
Yes, the odds are you could get one that way...if we don't count networking. The girls at the school will most likely have a wide network with each other and the boys will not know if X person is or is not a part of this network. When I was a kid, I had many problems with myself. There were some new boys at the school who decided to target me between classes. A few of the girls came and defended me by warning them that they will never get a date in the town. A girls network is a big deal and any male should be very aware of it.
Eh, the fact they network actually makes it more common
after a certain point, as it will be known that the relationship you are looking for is somewhat casual, and they don't feel like they have to actually
like you to give an affirmative response. Enough that they feel like your appearance is attractive enough, while holding some curiosity in dating or simply desire to be physical.