Back in the day, the customary question among Japanese gakusei (学生, students) around this time of year was "Natsu yasumi dō datta?" (夏休みどうだった？, How was summer vacation?). But that was in the days of no smartphones or Skype, when there was a lot less of this hankering for tsunagari (つながり, connectedness).
When schools let out for the summer, kids resigned themselves to being out of touch with friends and classmates until Sept. 1 when everyone reconvened in classrooms to say hello and swap vacation stories. That first day back felt so shinsen (新鮮, fresh) and new. Oh, we were digitally deprived of course, but on the other hand, think about the stress of needing to know what everyone is up to on an hourly basis, every single day, and having to broadcast one's own doings as well. Ma, iikedone (ま、いいけどね, not that it matters much).
Some things don't change though, like the fact that once a Japanese stops being a gakusei, it also signifies the end of their natsu yasumi (夏休み, summer vacation). Unless you're a student, it's pretty hard to get any sizable amount of time off and if you're unemployed, free time will cease to feel like a vacation. Either way, the average Japanese adult rarely gets to enjoy the Nippon no natsu (日本の夏, Japanese summer) in any true sense and zannen nagara (残念ながら, I regret to have to say) that modern life has done much to ruin summers for us all.