A/N: Takes place during 'Charges and Specs' in that time jump between the parking garage and Holt's office, right before the end scene with Amy. Written because I have feelings about his very casual mention of not knowing what will happen, and "if something bad goes down."
"And sign here." Jake's hand is getting tired, but he's not even halfway through the pile of contract papers in front of him. The FBI basically owns him now, and they're experts at making sure they don't get screwed over.
His paperwork when he joined the NYPD looked very similar to this, but it was only a third of the length. He's barely glancing over the pages as he signs them, but he doesn't need more than a glance to know what he's signing. Jake's hand is cramping, but it's nothing to the sinking in his gut.
The phrase not liable for is on almost every page, and next to it, he reads the most horrible life events he could think of, but he knows that because it's spelled out, it's happened to someone working with the FBI. His eyes flit over disfigurations, loss of limb, hearing loss, vision loss, other disabilities, and death. We are not liable for loss of life he reads over and over again, between the panic disorders, emotional trauma, and other maladies not herein defined.
Jake's always been serious about his job, he's always known that it was dangerous and that he could get seriously hurt or end up dead. But the other half of the agreement not involving death all circulate around maintaining an undercover status in which he only communicates with the FBI. He always thought that if he died on the force it wouldn't be so bad, because he would have his friends all around him, and maybe he'd even get a moment with Amy as he lay dying.
None of that's possible with the FBI. If he dies, it will be with everyone thinking he's a criminal, surrounded by criminals, and it will have nothing to do with an unfortunate weak spot in his bulletproof vest.
There are only a few more pages left for him to sign when his eyes catch on husband, wife, any life partner, descendents, or heirs and his hand actually stops. For a second he can't breathe, his heart pounding against his chest. He doesn't have a wife or any heirs, and it hits him then that he might never have a wife, or kids who would want to sue over his wrongful death. He signs anyway because he has to, because it's just a formality since there is no one who fits that description.
But it gnaws at him all the rest of the way through his briefing, through the small meeting in Holt's office, and the whole time he's cleaning out his desk. He might never have a wife or kids, but it's not because he doesn't want them. The pit in his stomach is insistent, and he knows the only way he's going to be okay dying without a wife or kids is to make sure the universe knows it was a possibility. He has to tell Amy that there could be a them, so maybe there still could be. Even if the only place they get to be together is in the imaginary "could have been" place that lives on after him.
It's not ideal, and it doesn't make him happy, but it's better than nothing. And that's just how it is.
A/N: I have never signed a contract or agreement where you agree it's not your employers fault if you die, but I'd like to think I know enough of the legal jargon to have been reasonably accurate about it. Also if you don't think Jake actively wants kids and would get bummed about it YOU ARE LYING TO YOURSELF and I will give you a list of canon reasons why.
Anyway, this is just my head-canon about Jake's character and the non-shippy part of why that scene makes me want to cry.