Rosh Hashanah and Labor Day? Thanksgiving and Chanukah? What is with the calendar this year, and how do I explain it to my non-Jewish friends?
This year's High Holiday schedule threw a wrench into many back-to-school scheduling plans and confused the heck out of Jews and non-Jews alike. We also, ultimately, went back to school, celebrated the High Holidays and managed just fine. The Thanksgivukkah phenomenon is both less inconvenient and more marketable , and the holiday mashup has gone viral . The way I see it, the coinciding Thanksgiving/Chanukah season is an opportunity for families to celebrate multiple holidays together and reserve the Christmas season exclusively for Chinese food and movies without any potential for a Jewish holiday to confuse matters.
Many Jewish professionals I know love saying things like, "The holidays aren't early — they're on the same Hebrew date every year!" This year, everything is early, and according to all the Internet sources I can find, Thanksgiving and the first day of Chanukah won't coincide again for 70,000 years. You might as well buy a T-shirt ; this is literally a once in a lifetime experience.
The Gregorian calendar is essentially a solar calendar: It takes approximately 365 days for the Earth to go around the sun, and we have an extra day added every four years to make it work. The Hebrew calendar is essentially a lunar calendar, with months starting with the new moon. In order to keep holidays in the right general season, an extra month is added to the calendar seven times every 19 years. Super straightforward, right? You don't have to understand it, exactly, but you do have to recognize the genius of whoever figured out this system! (The Muslim calendar is strictly lunar, so their holidays actually do move seasons.) This article  explains the nitty gritty calendar calculations in more detail.
As for what to tell your non-Jewish friends, how about a little rundown on astronomy? It's confusing, yes, but accepting that different traditions calculate their calendars and their holidays differently is a great lesson in diversity. You can explain that Chanukah is always on the 25th of Kislev, but that doesn't translate to the same exact time of year on the Gregorian calendar. If your Thanksgiving celebration will include any non-Jewish friends, they'll get a two-for-one holiday celebration. It's also important to communicate that the English dates will be totally different next year thanks to that leap month being added in. For anyone interested in when a Jewish holiday is going to happen, check the current year's calendar, not the calendar from the year before. (Chanukah starts on December 16 in 2014, in case you were wondering.)
Despite all the to-do about Thanksgivukkah, I'm sure retailers will still want to make their Christmas displays seem multicultural by including dreidels and chanukiahs. At the end of December, in between bites of Chinese food, I look forward to many mocking remarks about leftover Chanukah merchandise sitting around for a year. By educating your friends a little, at least they can get the jokes.