Age: Birth - 17
Dates: September, 1981 - August, 1999
Primarily raised by his sister after both his parents left before he reached the age of 14, Chuck spends his childhood overcoming a sense of guilt and inadequacy over his parents' abandonment, not knowing the true reasons they had to leave. He attempts to cause as little trouble as possible for his sister but, in the company of his best friend, Morgan Grimes, trouble is often easy to be found.
Age: 17 - 21
Dates: August, 1999 - April 2003
Encouraged by Ellie to apply to Stanford, Chuck is astonished to get accepted into their electrical engineering program. Daring to set his sights high, picturing a successful future in the tech world, it all comes crashing down when his roommate, Bryce Larkin, hides test answers in Chuck's room and gets him kicked out of school for reasons that Chuck wouldn't understand for years after.
Age: 21 - 26
Dates: April, 2003 - September, 2007
In a slump from losing Jill and the future he'd had planned, Chuck reluctantly agrees to work at a Buy More... at least he gets to spend time with Morgan. Though he has a few dates and gets promoted to Nerd Herd supervisor, Chuck starts to think that all his future holds is more of the same.
Age: 26 - 27
Dates: September, 2007 - April, 2009
Episodes: Chuck vs the Intersect through Chuck vs the Ring
In a single night, everything changes. Opening an email from Bryce, thousands of government secrets download into Chuck's head. Becoming a high level asset for the CIA and NSA, Chuck is assigned a pair of handlers, Sarah Walker and John Casey.
Age: 27 - 28
Dates: April, 2009 - October, 2009
Episodes: Six month period between Chuck vs the Ring and Chuck vs the Pink Slip
After downloading the Intersect 2.0, Chuck's puts being an asset behind him... by training to become a full-fledged agent. However, this choice also means walking away when Sarah asks him to run away with her.
Age: 28
Dates: November, 2009 - April, 2010
Episodes: Chuck vs the Pink Slip through Chuck vs the Other Guy
He'd thought that, as an agent, he and Sarah would finally be able to get together, but after what happened in Prague, she pulls away. With Sarah seeing the newest member of their team, Shaw, and Chuck dating the newest Nerd Herder, Hannah, Chuck and Sarah's chances of ever being more than partners seem dim.
Age: 28
Dates: April, 2010 - May, 2010
Episodes: Chuck vs the Honeymooners through Chuck vs the Ring: Part II
Finally a couple and finally a full agent, everything seems perfect... until the Intersect starts to malfunction, with obscure dreams, increasing migraines, and a threat of insanity.
Age: 28
Dates: May, 2010 - July, 2010
Episodes: Beginning of Chuck vs the Anniversary
Leaving the CIA and swearing off kung fu, Chuck picks up a mission of his own - figuring out what happened to his mother, an agent lost for the last twenty years. He and Morgan embark on an adventure across the world to find her.
Age: 28 - 29
Dates: July, 2010 - January, 2011
Episodes: Chuck vs the Anniversary through Chuck vs the Push Mix
Back with the CIA... and at the Buy More, Chuck joins Sarah and Casey on their investigation into Volkoff Industries... not knowing that his own investigation into his mother's disappearance will lead to the same answers.
Age: 29
Dates: January, 2011 - May, 2011
Episodes: Chuck vs the Push Mix through Chuck vs the Cliffhanger
In the midst of planning their wedding and with Alexei Volkoff behind bars, Chuck and Sarah come up against a new threat - Vivian Volkoff, Alexei's daughter and heir to his criminal enterprises.
Age: 29 - 30
Dates: May, 2011 - November, 2011
Episodes: The end of Chuck vs the Cliffhanger through Chuck vs the Business Trip
With the fortune left to them by Hartley, Chuck, Sarah, Casey, and Morgan open their own, private spy business. But with the Intersect in Morgan's head and their fortune frozen by the conniving Agent Decker, Carmichael Industries verges on collapse.
Age: 30
Dates: November, 2011 - January, 2012
Episodes: Chuck vs the Hack Off through Chuck vs the Bullet Train
With Casey arrested and the team framed for releasing the Omen virus, Chuck begins to suspect that his family might well be cursed. However, after learning that all their troubles trace back to Shaw and their past as spies, Chuck and Sarah start to realize that they don't want a future in the spy world, surrounded by the secrets and lies they'd sworn off long before.
Age: 30
Dates: January, 2012
Episodes: Chuck vs Sarah through Chuck vs the Goodbye
When their last mission goes wrong and Sarah downloads the faulty Intersect, Chuck faces his greatest challenge yet - getting a reclusive spy, who doesn't remember ever being loved, to fall in love with him again.
Age: 30+
Dates: January, 2012 to Present
Chuck and Sarah go up against the shadowy organization that kidnapped their daughter.
A note on the timelines: I've tried to be as accurate as possible with the dates. Some are concrete as it is explicitly stated when events occurred, with others I selected a date from an approximate range. I used the Chuck wikia timeline as a guide but found that they failed to take some time jumps into account and made adjustments accordingly.