Somehow emotionally wholesome but also emotionally lewd. She's giving him good advice and encouragement, but also kind of stringing him along playfully without making her intentions clear. The poor straightforward lad has no idea how much his view of the world has been reshaped around her.
@Richman
tfw no Onee to get you out of your house, seriously, i have never been invited anywhere since i started Highscool.
Believe me when I say this-- the best fun you can have in HS is just to learn to enjoy being yourself and finding hobbies you like. Don't be afraid to ask to join people for stuff, or invite others to go to events, movies, or the like, cause there's no point waiting around for someone else to do it. Worst thing that'll pretty much ever happen is you have an awkward memory to cringe and laugh about, and you'll probably be better off and happier for it.
Maybe don't go hit on older women on random streets to try and find one like this, though, that might get weird in any number of ways.