Okay, so, here’s what I picture:
Flynn has never been smitten before. Sure, he’s admired a few women in the past, but nothing past a fleeting affection or just general attraction. He’s a busybody and focuses more on work than anything else.
So, of course, he wasn’t looking for anyone, but he met Judith and things just kind of went haywire. He sort of figured she and Yuri would vibe with one another more since they were practically of the same breed, but Yuri never seemed to be interested in Judith past the friendship they shared, and Judith had always been unreadable from the start anyhow (so no brainpicking to be had there). She teased him in ways not too unlike how Yuri did, though she wasn’t infuriating about it. Somehow, he always ended up red-faced with his heart racing, but he figured it was because of his inexperience with flirting versus the smooth, no-beats-missed Yuri who seemed to match her perfectly.
Imagine this being still mid-game, maybe at Aurnion, when Flynn has joined the party permanently (iirc) and he’s had enough time to mesh into the group. He knows the others well enough by now, and he’s comfortable, but for some reason he’s still nervous around Judith. He knows that he’s fascinated by her (and, by all accounts, lost in the sauce for her) but he isn’t sure how to do it. He makes the mistake of trying to confide in Yuri, but all he gets is a slap on the back and a grin.
“Sorry,” he says, “but you’re on your own.”
He admits his feelings to Estelle next, and she’s thrilled. She thinks he should tell her before they go into this final battle. After all, there’s no telling what could happen…right? However, Rita (who had been eavesdropping) thinks it should wait. Dropping a love confession right before a battle? Isn’t that a bit heavy? If it weighed too much on her mind, surely it would throw her off and make her less useful in the fight.
“But Judith always keeps a level head in battles,” he says. It’s true, of course, but maybe he’s trying too hard to rush it.
He doesn’t tell her that night.
It’s when they’ve just beaten Duke, and they can hardly catch a breather when he blurts it out.
She’s standing beside him, supporting him as Estelle is healing a gash in his leg, and she stares at him as he starts to pour his heart out to her. For once, she looks like she doesn’t know what to say - but that’s because half of her attention is on the re-igniting Duke, and he can practically read the disbelief on her face, as if she were saying, seriously? Right now?
Everyone else is staring at him in shock - except for Yuri, who drops his face into his hand, shaking his head.
Duke waits for no one, and finishes his spiel even with the entire group distracted by Flynn’s babbled confession - and he once again attacks, igniting a battle even harsher than before.
After all is said and done, Flynn feels mortified by his impulsive admission, but as he’s winding down from the battle later on, Judith approaches him.
“My, what an exciting little speech that was,” she remarks, and he turns bright red.
“I-I’m sorry, Judith, I-”
She leans in before he can finish speaking, and his heart leaps up into his throat. “If you’re going to take me on a date, you really should start calling me Judy,” she hums, and he finds himself wordless, analyzing her words with the one or two braincells able to survive her charm. Her smile broadens. “It’s so cute, seeing such a composed leader with such a red face.” Her face is so, so close, and he can feel every gentle breath of hers on his skin, until their lips are almost touching.
His eyes slide shut with anticipation, and his hand slides around to gently touch her back and pull her in - but she pulls back at the last moment, running her fingers through his hair playfully instead. His eyes blink back open and he finds himself reaching for her, protesting the lack of contact.
Judith sits beside him instead, smiling sweetly; she knows what she’s doing to him, and seems to enjoy it, really.
He does his best to compose himself, pushing away his dazed look. “…how does dinner sound?“ It wouldn’t be perfect, considering what they had all just been through, but…
“Oh, I suppose I could make it.” Her hand slides to gently catch his, locking their fingers. “It’s a date.”