Current with canon; Annie's main verse, seen in SWS/SSWS/memebells.
Her past with Clay is that they dated for a year and a half, and broke up shortly before S2. Between then and whenever, their relationship has been like a dimmer switch: sometimes brighter than others, sometimes not. More FWB than anything, though currently they're in the "very dim" spot.
Her relationship with Auggie is currently in a weird place what with their recent missions. They flirt, they're very close and, in the past, have had a sexual relationship.
Future; For Clay in SWS/SSWS/memebells at whim, but also in journals.
See above: however, Jai didn't die; six years after their breakup, Clay's mother died and Annie found him in a bar; one thing led to another and they rekindled their relationship; six months later, they were married.
He's D-CIA and she's... well, Annie Walker-Webb.
Auggie is still a fixture in Annie's life - her BFF to the end. Plus, the Director of Central Intelligence buys his coffee. ;)
Her past with Clay is intact. Show canon mostly applies; he proposed to Parker and fought his feelings for Annie... until their mission in Barcelona and the pirates in Somalia happened.
He and Annie spent another night together and he broke off his engagement with Parker. They're going to see how things go. Hopefully, not too bad.
Simon & company is a go.