Around the Island

Back by popular demand — ‘Battle of the Brains’

Getting ready for reentry, but finding it tough to string two intelligent words together?

Then dust off the old thinking cap and put your smarts to the test. Join quizmaster Bob DeStefano for another Zoom-based “Battle of the Brains” on Friday, June 4, at 7 p.m. The thrill of victory, the agony of defeat — you don’t want to miss this chance to meet, greet and compete with your neighbors, all from the comfort of your couch (and maybe even in your pajamas).

Terry Lucas, director of the Shelter Island Library, says the most popular Friday Night Dialogue offered on Zoom this past year was Trivia Night with Bob DeStefano — by a long shot. You may ask yourself “Just who is this Bob DeStefano and why does everybody love him so?”

Well, let “long shot” be your first clue — the quick-witted man with all the answers is none other than the revered teacher of the perfect swing, Gardiner’s Bay Country Club’s golf pro extraordinaire for 50 years straight. (Quick — what’s everyone’s favorite color at Augusta? Chalk up one point if you guessed green.)

Bob would say though, that’s a “gimme” question. He’s more interested in the ones that provoke long stares into the distance and murmurings like, “I know I know this one!” or “Jeez, it’s on the tip of my tongue …” only to be followed by “Aw shoot, I knew that!” with a heavy sigh. Question selection is an art, according to Bob: “If they’re too hard, then who cares?”

What’s the origin of the word “trivia?” In Latin, it means three (tri) roads (via), or the intersection where the commonplace occurs. It also refers to the three pillars of classical education — grammar, rhetoric and logic — upon which all higher learning rests. So maybe not the best question, but interesting nonetheless.

“My favorite format is teams of four people. They put their heads together,” Bob said. “Literally. Laughter erupts at every table. The whole night is nothing but laughter.” He recalls wistfully the Friday nights before COVID-19 when “Battle of the Brains” took place in person and fans flocked to the library to face a grueling 50 questions. “It was pure joy.” And what did they do it for? “We gave out four trivia books to the winners, but mostly they came for the bragging rights, and the fun.”

How many teaspoons are there in a tablespoon? Pat yourself on the back if you answered three because Bob says you’d be surprised how many people get this wrong.

Zoom is a whole different ball (golf?) game. “I streamlined it to 25-30 questions, looking for a winning score of 21 or so. Trying to keep the screen time down to about an hour,” Bob explains.

Although he really misses being in the room with everyone, he sees some upside in being able to attract players from far and wide (geographically speaking) and admits the Brady Bunch format does allow for more team variety. Some players opt to fly solo, others pair up with their spouses, and occasionally a multi-generational family fills a single square.

Bob wonders if it might make sense, when things go back to normal, to make the program hybrid so people with mobility issues can still participate. And his dreams don’t stop there. “Imagine if all the East End towns competed with one another for a grand trivia championship. Wouldn’t you want to be on the Shelter Island team?”

Can you name the quiz game that’s the longest running on TV? Need a hint? Since 1961, high schools have sent their best students to vie for scholarship money on this show. If you said, “It’s Academic,” take a bow.

Bob has run monthly trivia programs at the Rogers Memorial Southampton Library for years. He has tailored special quiz events for garden clubs and other private parties. But Shelter Island is his home, where his heart is. Ms. Lucas says Bob has a steadfast group of loyal followers to whom she simply emails the Zoom links directly — there’s no question they will be in attendance.

Bob reciprocates by throwing in a Shelter Island question that most local people get. For example, he might ask what Island institution Mary Lou Eichhorn has run for the last 40 years. Lucky for you if shopping at Cornucopia is your secret pleasure and congratulations on winning one more point.

O.K. Consider yourself trivia trained. Start the summer off right. Join the Shelter Island team and show Bob some serious love. After all, he helps the community connect through remembering together, which is a very special gift indeed. And newcomers, don’t be shy — you always belong at the library.

Please register for ‘Battle of the Brains’ at least 30 minutes ahead of time by visiting the events calendar on the library’s website at For further information or assistance, contact Jocelyn Ozolins via email at [email protected] or by phone at 631-749-0042. All library programs are free to the public, however donations are gratefully accepted.

Next Up: On Friday, June 18 at 7 p.m. via Zoom, enjoy readings in tribute to the late Richard Varney, Shelter Islander and lover of poetry, at the Varney Memorial Poetry Program, organized by Virginia Walker.