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Nate is no wordsmith by far, but he's got through life on his wits mostly. His wits and a healthy dose of good luck. What he knows about words is that what you don't say can be just as important as what you do.
'I've been in a spot of trouble in my time', delivered with a smile gets around the facts. It's not a lie, it's avoiding judgment. Most people he has to deal with tend to admire some verve in their friends and/or acquaintances, or at least romanticize the underdog type he plays up on. Yet you never tell someone you've been in jail, unless you know they have been too.
He hates to think what Elena's mother makes of him - a state prosecutor with plenty of connections to her local PD - though the couple times he'd been in the same room they've managed civility primarily through lack of contact and he wondered if she was aiming for plausible deniability about what kind of man her daughter was engaged to. With her carpenter father he at least would've had something to talk about that didn't get him in trouble, a shared appreciation of artistry, but her dad had died long ago leaving Elena without one parent. Nate had never liked to admit that maybe they were mirrors; her with only her mother and him with only Sully (and that dark secret that maybe he, technically, had a father, if anyone dared categorize the man who'd abandoned him as anything of the sort).
'I can do that' and 'We ought to be able to manage it' and so many variations of those have been uttered by him over the years. All permutations on the theme of him not exactly promising to borrow/beg/steal an object for the client themselves per se. 'I could do that for you', with the words 'I won't' left off. He's never proud to double-cross anyone, but it is how it is in the business. If you don't prepare for it, more fool you. And Nate has been fooled plenty of times himself so it feels a little like they're just spreading the wealth out a bit more fairly in the end. A dodgy thieves meritocracy that is really the only way he knows how to function with any person who steps into his domain. It's survival. That's what makes it fair when you collect your words together beforehand and carefully meter them out to your advantage. Every sound that comes out of anyone's mouth should be part of the tune they're playing, a move in their game. He's been at it so long he sometimes forgets that isn't how a lot of people see it. They often don't see it at all and if they do, to them, it's a deception.
That's how Elena sees it. Sometimes, she willingly forgets, plays along in the game of his as a companion. She enjoys the challenge, the adventure, him teaching her his tricks. But when she's the competitor, and the treasure to win is being right, she'd remind him it's not a game between them, that arguments aren't meant to be fought that way. An irony he reckons, considering she's a writer and the former debate champion of her high school. She believes in justice then; in logic and the truth. Elena always has him over a barrel there because she can sense the omission. He resents it because he can't be right by her, except by doing right. His past isn't like that though, he's made a lot of decisions he's sure she'd disapprove of, and he can't change it now so there'd been this growing sense that he'd already failed her.
As he sips his beer, grateful for the shade of the hut, he thinks the worst thing he ever did was tell Elena the truth about him, laying pretty much his whole life out in front of her for her to know and secretly judge. It was all she asked for - all she needed she'd claimed - but he could never do it justice, never let go of those small parts of himself he needed to protect. Every time she asked for more he eked out a larger space held back, just because. It was survival. He'd been afraid. Of course she'd said that was why they hadn't worked out, but he'd only done it protectively, to be able to survive her, if worst had come to worst. Which it had, and he should've seen it coming. Arguably he had, if he counted his behavior as instinctual and therefore justified.
He orders a third beer as he waits for Flynn to show up, and thinks he failed both himself and Elena that way because their relationship certainly didn't survive, and he's not surviving all that well in the end. The jobs are a distraction, flashy and adrenaline-fueled, and ultimately only a temporary reprieve from the heartbreak. Part of him even feels wrong about the plan he's here to enact, standard as it is for someone like him. He's had that twinge before, but it's stronger today and now he blames Elena for her moralizing him – changing his perception from shades of grey to a stronger contrast. The annoyance there makes it a bit easier to push the idea down, accompanied helpfully by the alcohol surging through his system.
He's looking forward to working with Chloe again at least, and even good ol' Harry. Neither of them would say everything either, and none of them would expect too much from the others, which is what made this the perfect remedy for his woes. He could get back to who he'd always been in the company of semi-strangers who had as many secrets as him that he could feel comfortable with them implicitly. They'd never trust him fully, and he the same, but no one would accuse, an agreed silence comparable to a truce. It worked out almost better that way. Most of the time.