He spends half a decade hunting the man. Half a decade tripping over false clues and stale breadcrumbs. He watches Reddington slip around corners and into sleek black getaway cars. He watches him eat fine foods, buy new hats, and bed beautiful women as he jet-sets around the world, pulling the strings behind some of the worst crimes in modern history. He watches him live a full life even while he knows the police are hot on his heels, which only asserts to Donald that in reality, he and the rest of the FBI probably aren't that hot on Reddington's heels after all.
It makes him furious, this feeling of impotence. Things with Audrey go sour as well, and he starts to feel impotent in another department of his life, too. He works harder to catch Reddington so he can get his fucking life back, but it's all to no avail. Audrey leaves. Reddington steps his Italian leather-clad foot into another big black car. Donald flies back home in disgrace.
Not long after, Reddington strolls into their headquarters all on his own and demands to speak with Elizabeth Keen, and everything goes to shit.
When he ends up locked in the box with Reddington, his leg shot up to hamburger and the shock setting in, he thinks he's hit rock bottom. This is my life, and this is how it ends. Stuck in a government box with the man who ruined everything. When Reddington threatens to shoot him in the head to save Keen, Donald can't help but think, Oh, just get it over with. I'm too tired for this shit. But in the end, his will to live outranks his will to die, and he gives up the code.
Laying in the hospital doesn't do much to raise his spirits, but when Audrey walks in and takes his hand, he thinks maybe things are starting to look up. He knows that on some level, he has Reddington to thank for this, but he shoves the thought away and endeavors to never think of it again. It mostly works. But when Audrey's dead and Tanida's head's delivered on a bed of straw in a beautiful box right to his doorstep courtesy of the master criminal, the thought creeps in once more.
"Sometimes I think you destroyed my life," Donald tells Reddington shortly after his special delivery. They're sitting in Donald's apartment, drinking beer and not talking about their shared grief. "But then I think about the box and Garrick, and how it's because of that day that Audrey walked back into my life, even if it wasn't for very long, and I realize you didn't really destroy anything. Or at least, not anything you didn't somehow find a way to fix."
Reddington only takes a drink.
"She's gone now, again and for good, and I want to be mad at you. I spent so long being mad at you before when I lost her the first time. It feels natural to let all the rage come back now. But it...it doesn't stick. The image of Tanida's head sneaks in whenever I start to get mad at you, and the letter you wrote...." He can't think of what to say about the letter, so he says nothing. "I want to be mad at you, but I just can't be. Not about this anyway."
Reddington puts his beer on the coffee table. "Dembe didn't think the head was a good idea," he says as he folds his hands in his lap.
"It was perfect," admits Donald, his voice thick with grief and gratitude.
"I knew it would be," Reddington replies. "I knew that thirst for blood within you would only be sated with his death, and I knew you couldn't be the one to deliver the final blow. So I did it for you; forgive me if I was out of line."
"You weren't," says Donald, and he tries to keep his words even. "Thank you."
From then on, Reddington somehow manages to get into his apartment when he's not paying attention, and the pair share a drink. They don't talk much--they're mostly memorializing their dead and gone--but it's soothing in its silence.
One night Reddington stares long and hard at Donald, who's a few drinks past tipsy, before asking, "Have you ever had sex with a man, Agent Ressler?" and Donald almost chokes on his scotch.
"No," he splutters.
"Would you like to try?"
Donald laughs because he's not quite sure what else to do. He looks over at Reddington, who sips his own scotch with the same elegant poise he maintains regardless of whether he's charming some wealthy aristocrat over dinner or damning multiple people to death. Donald laughs again.
"I'm being completely serious," Reddington insists.
Donald's laugh stops abruptly. Even drunk he can tell that Reddington is, indeed, being quite serious. He has no idea what to make of that, so he says the first thing that comes to mind. "Have you ever had sex with a man?"
"Many times," Reddington says matter of factly. "I find it rather pleasurable. I prefer women, of course, but there is certainly something to be said for the male form. And yours is rather nice."
Donald blinks owlishly. "I'm not having sex with you," he says with a strangled voice.
Reddington scoffs. "Well obviously not now. I require sobriety before intercourse. But when you dry up and've had a bit more time to consider my proposition, give me a ring."
He's furiously trying to figure out how he got here in the conversation. He's not even sure when or how Reddington got into his apartment, let alone how on earth they've arrived at a point in the discussion where they're casually talking about fucking each other. Or at least Reddington is casually talking about fucking Donald. Donald isn't casually talking about anything so much as he's desperately trying not to vomit thanks to the sudden jolt in his stomach.
When he looks back towards Reddington, still scrambling for a response, he finds Reddington has already left. But on the coffee table is a small slip of paper with a phone number written on it in a small neat script. He wonders briefly if this is the same number Keen has access to, but then he has to run to the bathroom and that train of thought stops just short of the station.
When he sees Reddington again, it's at the Post Office. He has no idea how to react to the man, so he sticks to his guns and gives him all kinds of attitude. It's easy considering how on edge Reddington makes him. But the man doesn't seem to care about Donald's poor behavior.
"Is this how you flirt?" he asks with a bemused smile. "It's quite ineffectual, but I appreciate the effort." Then Reddington strides away towards Cooper, leaving Donald to breathe heavily through his nose and clench his fists together while Liz stands off to the side and gapes like a fish.
"What the hell are you looking at?" he snaps at her, and she puts her hands up in surrender and shakes her head.
"Not a single thing," she replies, but she's snickering. Donald wants to punch something. Preferably Reddington.
When he gets home that night, there's a package on his doorstep. It's a $75,000 bottle of Macallan. There's also a note: "Please, I beg of you, don't drink this all in one sitting like the last time."
Donald's tempted to leave the bottle on the doorstep, or perhaps throw it out his kitchen window--he's certain Reddington's watching somehow--but he tamps down the urge and simply takes the bottle inside with him. He doesn't open it though.
The next day at work Liz asks him to grab some lunch with her.
"I'd rather not, Keen." Donald says.
"Mm, not going to take no for an answer," she says apologetically.
Donald remembers vividly how Liz stabbed Reddington in the neck with a pen and decides not to challenge her.
They head to a diner down the street. Liz orders a salad, Donald a BLT. He says nothing, simply waits for Liz to get her thoughts in order.
"So, you and Red," she finally says.
"There is no 'me and Red'," Donald counters quickly. Liz gives him a look. "Liz, c'mon, please," Donald tries again. "I'm pretty sure he's just found a new way to make me uncomfortable."
"Seems like it's working pretty well."
Donald puts down his sandwich. "What do you want me to say? I don't get approached for sex by criminal masterminds all that often."
"Not by men much either?" Liz asks.
Donald sighs. "And not by men much either," he agrees.
"You thinking about saying yes?"
"Jesus, Liz, does it really look like I want to talk about this? What about you? You ever fucked him? Let's talk about that."
Liz's mouth tightens. "There's a really good chance he's my biological father, so no. I haven't had sex with him."
Donald wants to disappear. "God, I'm sorry."
She smiles. "It's fine. I guess I had it coming."
"Anyway, no. I'm not thinking about saying yes."
Donald can sense a "but" coming.
"But I have to say, I have always wondered. From a completely objective perspective obviously."
Donald glares at Liz over the booth table. "Are you giving me permission to have sex with Reddington?" Liz doesn't say anything. "Okay, first off, I don't need your permission, Keen. Second, I'm not even remotely considering having sex with fucking Reddington."
"That's a shame," comes a voice from somewhere behind him. Liz looks exasperated, but also somewhat amused, at the newcomer. Donald wants once again to disappear.
"Go away, Reddington," he groans.
"Hi, Red," says Liz with a small wave.
"Hello to my two favorite FBI agents," Reddington says with a smile. "If you'll let me join you I'll buy you both lunch."
"Please, take a seat," Liz says at the same time that Donald says, "I'd rather you didn't."
Reddington slides into the booth next to Donald and orders a burger. Donald pushes his plate away, appetite gone.
"How have you enjoyed the scotch?" Reddington asks him. Liz's eyebrow shoots up.
"It makes for real nice lighter fluid," Donald grits out.
"You know, actually I think I'm going to head back to the office," Liz says as she slips out of the booth. Donald gives her a desperate look and tries to follow, but Reddington doesn't budge, so Donald can't get out of his seat.
"It was lovely to see you, Lizzie, as always."
"I'll never forgive you, Keen."
Liz salutes and takes her leave.
Reddington turns to look at Donald. "What are you doing Thursday night?"
"I'm not sure, but I know something will come up."
"Have dinner with me."
"Am I really so terrible?"
"Yes. Without a doubt."
Reddington huffs. "I'm not sure what I've done to deserve this treatment--"
"Besides threatening to kill me, murdering Liz's father, contributing to or outright committing the killing of thousands of people."
"--but I really don't think this brusque attitude towards me is warranted."
"Well, we both know I beg to differ."
"Is it because I'm a man, or because I'm me? Or a bit of both?"
Donald squirms. "I'm not talking about this."
"A bit of both, then," Reddington concludes, but then his food appears. He asks the server to box the food up to go and then stands from the booth.
"I'll go pay for this and let you escape. I'm sure I'll see you later."
Donald books it out of the booth. "Unfortunately," he mutters. Then he walks quickly out of the diner.
Reddington shows up at his apartment on Thursday night with mountains of Thai takeout and a six pack.
"I thought it'd be easier to get you to have dinner with me if we didn't have to go out to get it. Also I wasn't sure what you liked, so I ordered a wide variety. This little Thai joint down the street from the house where I'm staying is really just heaven." Reddington pushes his way in past Donald, who is too surprised to do more than shut the door behind him.
"I'm allergic to shellfish," he says flatly.
"Oh, I knew that already," Reddington says as he arranges the various containers. "I'm not completely ignorant. Please, Donnie, take a seat."
Donald frowns at the nickname but takes a seat on his couch. "Did you buy the entire restaurant?" he asks incredulously as Reddington continues to take out containers from plastic bags.
"Just about. Except no seafood and no pad Thai, because I'm assuming your tastes are slightly less plebeian than that."
Donald huffs. "I like pad Thai."
"Then I despair," Reddington says sadly. "Here, try the taro-corn fritters."
Donald ends up trying everything, much to Reddington's delight. They're so busy eating that they don't spend too much time talking, but the silence is oddly comfortable. Reddington is lounging in Donald's armchair, eating his glass noodle soup delicately with chopsticks, and Donald can't help but stare. This man is trying to seduce him. This king of crime wants to have sex with him. He can't quite fathom it.
"You're wondering, 'Why me' aren't you, Donald?" Reddington says between bites.
Donald doesn't deny it.
"Well, to be honest you caught my eye back when you were bleeding out right in front of me. All that righteous anger about protecting me, and then it's all immediately undercut when your leg gets blown to bits. Suddenly I was the one protecting you. Now who saw that one coming?" Reddington places his empty container on the coffee table and crosses his legs. One hand rests in his lap while the other arm bends at the elbow so his other hand can rest delicately against his temple.
"You have my blood in you now. I'm part of you. And that intrigues me too. Then the nasty business with Tanida happened, and you were so hungry for your revenge. And I saw in you what I harbor in myself. And that starving beast lying in wait just beneath your skin howled, and my starving beast came forward and howled back. You and I are not the same in many ways, but in a few important areas, I think our true selves run parallel."
Donald swallows. Licks his lips. Feels his jeans grow unexpectedly tight.
"I can handle rejection, even with how few times I'm forced to face it. But I can't stand never knowing, and I refuse to keep from finding out. So here I am, FBI Agent Donald Ressler, in your living room, plying you with good food and good drink, hoping that by the end of the night you'll let me put my hands to the sides of your face and my lips flush along your own. I want to kiss you long and deep, likely how you've never been kissed before, though I do hate to brag, and I desperately want you to let me. But first, how do you feel about classical Hollywood cinema? I've brought a great Cary Grant film with me tonight." Reddington stares expectantly.
Donald's mouth is completely dry, and he finds himself at a loss for words.
"I'll take it you don't have much an opinion at all. That's fine; we can watch the film and then discuss." Then Reddington is out of the armchair and clearing away the empty Thai containers and setting up the DVD player. And then he's taking a seat very near to Donald on the couch and starting the movie.
When it's over, Donald still has almost nothing to say. He hadn't been able to focus much on the movie, what with Reddington plastered up against his side so that Donald could feel intimately every laugh and sigh that Reddington expressed as the film played. But he hadn't been able to tear himself away either. Even now with the movie finished, Donald finds he's unable to move. The credits roll and Reddington turns to him, waiting for some kind of response, and all Donald can say is, "I have no idea what just fucking happened."
Reddington laughs. Then he adjusts so that he's facing Donald on the couch. "I'm going to kiss you now, Donnie," he says, and Donald can only swallow. "I need you to nod if that's acceptable." Donald's head offers a minuscule jerk, but it seems to be enough for Reddington. He leans in, placing his hands, as promised, on either side of Donald's face, and then gently presses their mouths together.
It is immediately too much for Donald, who abruptly stands from the couch and wipes at his lips. "Okay, I need you to leave now."
Reddington looks disappointed, but he nods all the same and stands from the couch as well. "That's perfectly all right, Donald," he says. "Perhaps another time."
I don't think so, Donald says silently to himself, but he can't bring the words into audible being. Reddington says goodnight, but Donald says nothing in return, and when Reddington leaves, Donald doesn't bother cleaning anything up further. He just makes a beeline for the bathroom and brushes his teeth before crawling into bed where he is completely unable to fall asleep.