"I don't think I'll ever be ok, I don't think so," said Okrent's mother, Lynn Pollack.
It's not hard to understand why family and friends loved Okrent so much.
"He was loving, bright, driven, ambitious, passionate about his beliefs and willing to work on them," said Mike Okrent, Alex's father.
"He was the kind of kid who would never forget a birthday, always made an effort to be with us when he could, hugged us when he saw us, hugged us when he left," Pollack said.
After finishing up a morning boot camp workout, Okrent headed into work at President Obama's campaign headquarters in the Prudential Building downtown.
He was chatting online with a friend, when he told her he wasn't feeling quite right.
He walked away to take an aspirin, collapsed on the floor and died.
His family believes he died of a massive heart attack.
"They said they worked on him for over an hour, but they never got a heartbeat," Mike Okrent said.
As their family and friends gather to support them, Alex Okrent's boss, President Obama, reached out to the family as well.
"It was very nice," Pollack said. "He sounded genuinely sympatric and also aware of the loss that Alex would leave in the campaign."
Okrent has been with the president's team since he was a senator, traveling with the campaign all across the country, finally coming back home to Chicago to work as the campaign's media director in January.
His family is now left to deal with not knowing what he could have been.
"I only think of how much more he could have done and would have done and how many experience in life he didn't get to have," said Pollack.
The family is expecting 500 people to attend Okrent's funeral Monday morning at the Jewish Reconstructionist Congregation.