Shocker: I don't own the characters from "The West Wing".

Set during "The Portland Trip", Josh reflects on his evening.

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"Actually, you have no sense about these things. You have no vibe, you have terrible taste in men, and your desire to be coupled up will always and forever drown out any small sense of self or self-worth that you may have."

Man, he'd been dying to get that off his chest. But as soon as the words had left his mouth, he'd felt a twinge of regret. The hurt look that had crossed Donna's face for a second before she'd bounced back with the "Deputy Downer" crack had made him wonder if he'd gone too far. Which, of course, he had. It wasn't his place as her boss to be critiquing her dating life.

Still, it was true, wasn't it? Even if it had stung, maybe it was something she'd needed to hear. His frustration with Donna's revolving door of gomers, and the undeserved level of importance they seemed to have in her life, had been simmering under the surface ever since she'd first come to work for him. Whether it was dropping out of school to pay Dr. Freeride's tuition, or walking away from a presidential campaign that was just starting to gain momentum because Freeride had decided he wanted her back, or chasing after every Donald and Todd and…

Todd. What kind of a name was Todd, anyway? He pictured a tall guy in a suit, good-looking in a plastic sort of way, with slicked-back hair and a phony smile. He was an insurance lobbyist; didn't that say it all? And Donna thought he might be 'the guy'? The guy? After meeting him once? Josh felt his blood pressure start to rise.

He should have let her have her date, he admonished himself with a pang of guilt. He could have gotten along without her for the evening. Really, all that had been on his agenda was trying to convince a gay congressman that a bill restricting gay marriage was a bad thing; in a sane universe, it would have been the biggest piece-of-cake meeting he'd had all month. God, he wanted to shake Matt Skinner. He really should have pointed out that the fact that Matt was defending the Marriage Recognition Act completely invalidated his NRA analogy. It would be as if the three million anti-gun activists joined the NRA and then voted in favor of guns. He would have thought to mention that inconsistency, except that ever since Rosslyn, any mention of guns seemed to interfere with his ability to think clearly.

Anyway, yeah, he could have let Donna off the hook. He'd actually been thinking of relenting when he'd sabotaged himself with "if you want to have sex, you'd better do it during dinner." The image of Donna having sex with this 'Todd'…gah, why had he even let his mind go there?

But she needed someone to look out for her, he reasoned. She was still relatively new in DC. She'd lived here for less than two years, and it was a world away from Wisconsin. And she was so trusting. She needed a big-brother type to protect her from the sleazy sharks that populated this town. Guys like Todd and Donald…he knew their type. All they saw when they looked at her was a blonde with a great body. Or they saw someone with White House connections who could be used to further their own personal agendas. They didn't see, or care, who she really was: a smart, quirky young woman with a freakish knowledge of trivia, who wasn't shy about arguing policy with Josh or Leo or the President of the United States when she disagreed with something they were doing, who had tried to organize a work slowdown among the assistants to promote ergonomics regulations. They didn't see the woman with a heart of gold, who – if something bad happened to you, if you got shot – would refuse to leave your side during your recovery. Josh squeezed his eyes shut, quickly forcing thoughts of the shooting from his mind as a familiar sick feeling began to come over him.

Big-brother type. Was that really how he saw his relationship with her? In his heart, he knew it wasn't. He wasn't all that good with women – okay, that was an understatement – but the way he felt when he looked at Donna was impossible for even him to misinterpret. But it didn't matter. She worked for him; there was nothing he could do about it. Making any kind of romantic advance toward her would put him firmly in the same category as the scumbags he wanted to protect her from. In fact, it would make him worse than those guys. He would never do that to her.

…Later in the evening…

"You look really great in that dress tonight, Donna. You should buy it for yourself."

It had been his way of apologizing for having been a jerk that night, and for ruining her date – though he'd be lying if he said he hadn't been thrilled to hear that the date had bombed on its own. So much for Todd being 'the guy.' And it had also been his way of trying to tell her how special she was, without crossing any lines that shouldn't be crossed.

And of course, it had also simply been an undeniable statement of fact. He wondered if she'd bought his act earlier about not having noticed the dress. As if Donna walking around his office in that stunning red thing was something he could miss. But noticing the dress would have meant also noticing that she had plans for the evening, probably with a guy, so he'd tried his hardest to ignore it.

Maybe someday things could be different between them. Maybe after President Bartlet's second term was over…Josh knew that was a fantasy. Surely by then a woman like Donna would have found someone else, someone who wasn't such a gomer. By then she'd probably be married with kids. But if she wasn't, and if she could ever bring herself to be attracted to a middle-aged man with a receding hairline…

However unlikely that possibility was, it was enough to put a hint of a smile on Josh's face as he left the White House grounds and began the walk back to his condo, softening the blow of an otherwise grueling day, in which he'd had to tell the President he would have to capitulate on a gay-bashing bill, in which Donna had said some loser named Todd might be 'the guy', and in which Matt Skinner had flummoxed him with a mere mention of the NRA.