It turns out a lot more than most of the rest of us.
Gross, 65, has started to make up for the five years he spent imprisoned in Cuba by traveling abroad, attending the State of the Union address as a guest of the Obamas and last week meeting Pope Francis
at the Vatican to personally thank him for his role in helping to win Gross' freedom.
After five years of being disconnected from the outside world, Gross now frequently posts on social media, writing of family reunions, eating the foods he longed for in prison and the reminders he experiences of his time in Cuba.
"I can't get away from Cuba," Gross wrote after hearing a Cuban song playing in an airport on his travels. While visiting Israel, he posted a photo of Cohiba cigars advertised for sale in a Tel Aviv tobacco shop.
In 2009, Gross was arrested by Cuban state security agents and eventually sentenced to 15 years in prison for importing banned communications equipment to the island.
Gross said he was merely helping the island's small Jewish community get online, but Cuban officials accused of him being part of a U.S. government plot to destabilize the island's single-party Communist government.
has highly restricted Internet access, and most people are not able to access the Web in their homes or on their phones.
On December 17, 2014, Gross was freed, along with three Cuban intelligence agents and a Cuban man convicted of spying for the United States. It was part of a deal between the Cuban and U.S. governments to reestablish diplomatic relations after five decades of Cold War animosity.
Gross, his wife, Judy, his attorney and three U.S. congressmen flew from Havana to his home state of Maryland aboard a U.S. military jet, one of the smaller versions of Air Force One used to transport President Barack Obama
The image of Gross celebrating his freedom aboard the flight home with CNN reporting the news of his release on a TV screen in the background became the picture he would use on his @AlanPGross Twitter page
A tasty return to freedom
The night of his release, he enjoyed a meal of spicy Thai food with family and friends, a far cry from the bland rations he was forced to eat in prison.
In January, Gross changed the status of his Facebook page to read that he had left his job as "hostage" at the Carlos Finlay military hospital where had been held in Havana.
Later, he shared pictures of a visit to the dentist's office to replace the teeth that he lost while he was held in Cuba.
With his dental concerns met, he moved on to food.
Gross also recounted savoring long-denied bowls of chili and bagels loaded with lox and cream cheese.
Many of the posts are the daily jottings of a man returning to his life after an extended absence: Gross renewing an expired driver's license or visiting a Starbucks for the first time in five years.
But in other posts, he writes about taking in a sunset on the beach in Israel, seeing the snow fall in Washington and believing citizens in every country should have unimpeded access to the Internet.
A spokeswoman for Gross turned down a CNN request for an interview with him but confirmed that the social media accounts are his.
Rep. Chris Van Hollen, the Democrat representing the Maryland district Gross hails from, called it "incredibly moving" that a man who spent five years in a Cuban prison has since sat next to first lady Michelle Obama and met the pope. More than that, he's come to signify the changing dynamics between officials in Washington and Havana.
"Alan did not ask for this special role in history," Van Hollen said, "but he's become a catalyst for this new chapter in American and Cuban relations."
The photos that Gross posted online show a smiling man, slowly putting back on some of the 100 pounds he lost in prison, no longer the gaunt-faced, hollow-eyed prisoner who had gone on hunger strikes to protest his conditions while he was held in Cuba.
"The distance we've come since December 17th 2014 has been a rewarding journey," Gross wrote in a Facebook post Saturday.
"For which we're grateful."