How does a country rebuild relationships with a former antagonist without alienating some of its own citizens who lost property at the hands of that former adversary?
Some Americans will find out how to do that delicate dance soon enough.
The relationship between the United States and Cuba went into a deep-freeze following the Cuban revolution of 1959 when Fidel Castro overthrew Fulgencio Batista, the dictator of Cuba.
Cuba then confiscated property belonging to thousands of American citizens and companies.
Those who lost their property all those years ago are now hoping that the new relationship between Cuba and the U.S. Can help them retrieve long-treasured belongs.
"All of our stuff was taken. I didn't have a bounce back from that. I mean honest to goodness, we were ripped off," says Cuban property claimant Carolyn Chester.
And while one legal expert says he's not sure if anyone who believes that they can reclaim long-exiled Cuban property really has very much chance of getting much in return, another expert seems sympathetic to what was lost in Cuba.
"When that happens, we're looking at the largest bankruptcy of the 21st century, ninety miles off our shore," says Michael Kelly, of Creighton Law School. "It could be as little as pennies on the dollar depending on what it is or it could be almost the full amount."
"I just want a little something that I can have for my son, you know something that I can have in the bank to help me fix my crooked steps," Chester continued.
Earlier this year, the Obama administration announced a relaxing of trade, travel and financial restrictions against Cuba, aiming at more long-term commercial and diplomatic ties between the U.S. and the island nation.