The chances of your character scrawling words across a piece of paper are getting less and less likely. Well, depending on the age of your character and how tuned in you are to that generation's traits.
This year's Beloit College Mindset List says that writing in cursive is one of those things the class of 2014 just doesn't do. (And I can attest to that. While my oldest learned cursive in second grade, both my younger two rolled right through the early grades without it. I'm told it's a less-than-useful skill in these modern days and precious curriculum time can be devoted to some other subject.) But back to our topic.
The references we use as writers to frame setting are often mired in tiny details like planners for work, post-it notes on the fridge, CDs in drive time. But depending on your target reader, they might be accustomed to a life with PDAs, text reminders, and those fancy iPod hookups in the car. Your assumption that you're on the pulse of the times might totally disconnect your reader from the story and compel them to write you off as old-fashioned or not their type of author.
Admittedly, we can't predict every new tide changing times bring. For example, I was reading a Dean Koontz book last year (sorry, can't recall which one), and a single character action snatched me out of the story: There was a doctor in a hospital and he went into the lounge to have a cigarette.
I immediately turned to the front of the book and searched for the copyright. I found that the book had originally been released in 1972 (or thereabouts), which explained why the doctor was lighting up in the hospital. We all know that doesn't happen nowadays. In fact, I know of at least one local hospital that prohibits smoking anywhere on the property. Obviously, smoking was still 1950s cool when Dean penned that manuscript. Who knew that two decades later it would rank right up there with the plague? lol
So, we should -- I think -- do what we can as authors to remain timely, yet timeless, and true to our characters. That takes research, social perception, and a little leeway from readers if we're blessed with Dean's longevity.