But while the talks present the best chance for a peaceful resolution to the chaotic demonstrations that have convulsed the city and divided its residents, they are unlikely to yield major concessions given that the government and protest leaders remain poles apart.
"The start of talks is not an end in itself," said Anson Chan, a former senior government official.
"Only the government can break the current impasse. It must show the leadership that has been totally lacking in the past three weeks, by coming to the table with proposals that offer genuine and substantial reform."
But this seems unlikely.
Beijing unlikely to budge
Hong Kong Chief Executive C.Y. Leung has said repeatedly that he would not step down -- a key demand of protesters.
Nor, Leung has said, is Beijing unlikely to budge on its prescription for electoral reform in the city and offer the kind of democracy protesters are seeking.
Even the moderator of the talks, Lingnan University President Leonard Cheng, warned not to expect too much:
"I'm not going to speculate at all about whether there will be a resolution," he said on Monday, adding that this would not be the only round of talks.
Five representatives from the Hong Kong Federation of Students including Alex Chow, the group's secretary general, and his deputy Lester Shum will meet with Chief Secretary Carrie Lam, Hong Kong's second in command, Justice Secretary Rimsky Yuen and three other senior government officials or advisers.
The talks begin at 6 p.m. local time and will be broadcast live from The Hong Kong Academy of Medicine in an event that will likely have the city's seven million residents gripped.
Some say they will hold viewing parties and the talks will be live-streamed to crowds on big screens set up in some areas -- including Mong Kok, a busy commercial district that has seen some of the most violent confrontations between demonstrators, police and residents that oppose the protests.
Poor can't be trusted?
On Monday, Leung offered a controversial defense
of Beijing's plan for elections in the financial capital, telling foreign media that an open nomination process would give the city's poorest residents greater influence over the political system.
"You have to take care of all the sectors in Hong Kong as much as you can," he said, according to the New York Times. "And if it's entirely a numbers game and numeric representation, then obviously you would be talking to half of the people in Hong Kong who earn less than $1,800 a month.
"Then you would end up with that kind of politics and policies."
His comments are likely to rankle the protesters and their sympathizers given Hong Kong's yawning wealth gap and a widespread perception that the current system of government is stacked against ordinary citizens.
One possible concession the government could make to immediately defuse tensions would be to re-open Civil Square -- a fenced off courtyard outside central government headquarters that students stormed at the end of September, triggering the unprecedented protests.
There is also still some possibility of give-and-take on electoral reform, such as allowing more democrats on the nomination committee or by promising to introduce greater democracy in elections slated in 2022.
The framework proposed for the election of the city's next leader in 2017 will allow registered voters to select their leader, although candidates must be approved by a committee that critics say will be stacked with Beijing loyalists and not be representative of Hong Kong.
Currently, the chief executive is elected by a specially-appointed 1,200-member election committee.
However, even if the talks yield concrete concessions, there is no guarantee that the protesters on the streets will go home.
There are several protest groups and it's not always clear who calls the shots or whether Hong Kong's young protesters will listen.
"I would want C.Y. to step down and for the government to show that they are sincere," protester Janice Tung told CNN.