I do think Astarion would go for Gale, if there were no Tav or Durge.
I can see the argument for him not using seduction at all if he's in charge and that's completely valid--the argument is that he feels safer and more secure because of his position, so he doesn't feel the need--but the whole leader position is a bit contrived to facilitate game mechanics. I prefer to think of the group as a team.
Even if he is the leader, though, he still needs people to stay with him. He doesn't think he has anything worth sticking around for. He knows his nature is off-putting to people and would still feel the need to hide it--you can reveal it whenever you want if you're playing as him, but I don't think he'd do so right away.
Now, his choices.
Shadowheart is evasive and suspicious of everyone. Lae'zel is a gith who might be good for a night of blowing off steam, but she's rough (certain dialogue indicates that although he can take it, he prefers a softer approach) and she's planning on leaving for the astral realm when everything is finished. (This is pretty clear from the beginning.)
Karlach is literally on fire and her future is uncertain. Wyll is sweet and attractive, but is also a monster hunter who gives him shit for his dietary needs. Halsin isn't an option right away.
You could argue that he would side with Minthara and choose her, and that's a perfectly plausible outcome but it also makes me sad. He'd probably do that on his own, but what if he doesn't want to lose the support of Wyll and Karlach? What if he's not the one solely capable of making decisions for the group?
So, although she might actually be the most in character pick, let's put her aside.
Gale is annoying to Astarion, but he's also a (former?) archmage whose only goal is to get back home to Waterdeep. He's patient, he admits fault pretty readily, he wants to help, and he can be surprisingly willing to indulge in darker things.
I think Astarion would find him interesting. The bomb would throw him for a loop, but by that point he's committed to the ruse and not quite willing to back out yet. He might insist Gale leave at first, but when Gale pleads for magic items and insists he has it under control, he could probably be coerced.
Gale is still the safest bet. Powerful, knowledgeable, willing. He can tolerate the rest for the sake of safety and comfort... until he actually grows fond of the wizard.
He'd probably be even more unhappy about that, honestly.
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@pandoraspearls: Maybe something about ash forgetting/not caring about his birthday but eiji surprises him with something small that reminds him he’s loved ?
Eiji memorized Ash's birthday the moment he saw it, of course.
It was when Ash was in prison—Eiji got to look over the paperwork, and Ash's birthday was listed under his file.
August 12th.
It's soon.
Eiji's a little worried about what to get for Ash. He doesn't want to throw a big party or anything. He doesn't want to gift anything too extravagant, either. Honestly, he's worried about it being triggering for Ash. But he wants to do something.
Ash's birthday is going to hit while they're on the road, Eiji realizes. This road trip is going to take at least a week, and Ash's birthday will happen toward the end, right before they reach Los Angeles.
At every gas station they go to, every time they make a pit stop, Eiji keeps an eye out for something he can gift to Ash. But they're always together—not that Eiji is complaining—and Eiji has no idea what to get him.
"Shorter," Eiji hisses one night, shaking Shorter awake. Ash isn't in the room. As much as Eiji thought Ash would be the type to sleep constantly, Ash barely seems to sleep at all in these motel rooms, instead catching rest where he can during the drives. "Shorter!"
"Whatdya want?" Shorter groans.
"What are you doing for Ash's birthday?" he asks.
Shorter sits up, rubbing at his eyes. "Huh?"
"Ash's birthday. It's this week."
"It is?" Shorter asks.
"August 12th?" Eiji asks, panicking suddenly. Did he somehow misremember? "Isn't it?"
Shorter shrugs with one shoulder. "I dunno man. He's never told me shit like that."
"... Oh," Eiji whispers. "Do you think I should—not do anything, then?" He honestly thought that Shorter would at least know of Ash's birthday, even if he didn't have anything planned. But for Ash to have not even told Shorter ...
But Shorter smiles. "Honestly, Eiji, I think you could do whatever you want and Ash would still look at you the same way."
Eiji tries not to flush. Does ... Does Ash look at him a certain way? He reigns himself in from asking how how how does Ash look at me?
"Right," Eiji mumbles. "Okay then. I'll get him something. Maybe just ... something small. So that he knows that I care."
"And I'm going back to sleep," Shorter declares, flopping back down onto the bed.
Careful not to further disturb Shorter, Eiji gets out of bed. He's going to look for Ash.
He finds him, and a part of Eiji feels like he'll always find Ash, even when Ash doesn't want to be found. Like right now, maybe.
Ash is sitting in the motel lobby—it's a shitty, broken down place next to the highway, but it's what they could afford.
Ash is in the corner with his back against the wall, where he can see people come and go. He's watching everything and everyone in the lobby with a hawk's—or, well, a lynx's eyes.
He spots Eiji immediately, of course, and seems to make himself even smaller when he does. Still, Eiji smiles and approaches him.
"What're you doing down here?" Eiji asks softly.
"Watching," Ash says simply.
"Watching what?"
Ash hums. "People."
Eiji rubs at his eyes, still tired. "People come and go even this late?" he asks.
Ash nods sharply. "They're the ones you have to watch out for," he says absentmindedly. "People get more brave in the dark."
"I'm not sure what you're talking about," Eiji admits, ashamed. Ash smiles softly at him.
"Go back to the room, Eiji," he whispers.
"Not without you," Eiji says back, resolute. He sits down next to Ash, making it clear that this isn't up for debate.
Ash shakes his head, but doesn't force Eiji to leave. He looks back out over the hotel lobby, and Eiji still isn't sure what he's watching for, but his expression is far colder on the lobby and the receptionist behind the window than it is when he looks at Eiji.
Uncomfortable, Eiji avoids looking at Ash's eyes. He doesn't like seeing Ash that way, even if he's not really certain what way that is. Instead, he looks down at Ash's hands, pressed together in his lap. There's something he hadn't noticed before—a ring of even lighter skin all the way around both of Ash's wrists, like they've been rubbed raw far too many times.
Eiji rips his eyes away, not wanting to dwell on that either.
"I, um—" Eiji blurts after a moment. Then, "I don't know what to get you for your birthday," he admits.
Ash blinks. "What?" he asks. His expression goes neutral now, and Eiji's not sure if that's an improvement.
"I still want to get you something!" Eiji says quickly. "I'm not giving up."
"You don't have to get me anything," Ash says, almost laughing. "What's got you thinking about my birthday, anyway?"
"It—it's soon, isn't it?" Eiji asks, again wondering if he somehow got the date wrong.
Ash shrugs. "Dunno."
Eiji blinks. "What?"
"I have no idea. I haven't thought about it in years."
"You ... don't know what day your birthday is?" Eiji asks. "Even if you don't celebrate it, don't you have to, like, put it in when you fill out forms and stuff?"
Ash looks over at Eiji, then away again. He shrugs. "I have to put in the date that matches whatever fake ID I'm using at the time," he explains.
Eiji flushes deeper. "Oh," he breathes. "So you really don't know when your birthday is?"
Ash chews on his lip for a moment. "I could probably remember if I tried," he admits. "Just haven't thought about it much in a while. I think the last time I celebrated it—" He cuts off suddenly.
"What?" Eiji asks gently, pressing just a little.
"I, uh—when I turned sixteen." Ash averts his eyes, looking anywhere but at Eiji. "Old man Dino got me a car." He wets his lips. He's nervous, Eiji realizes. He doesn't like talking about this.
"That was only two years ago," Eiji says. "You don't remember the date?"
Ash shrugs. "It was hard to keep track of days back then," he whispers. "Dino knew, but I didn't. And the car, it—it's not like I asked for it."
It slowly, slowly dawns on Eiji what Ash is saying.
He didn't ask for it. He's talking about more than the car, isn't he? He's talking about what he had to do to earn the car.
"Oh," Eiji breathes. "I—I'm sorry, Ash."
Ash's eyes go hard again. "This is your last chance to fuck me while I'm still underage," he mumbles.
"What?" Eiji gasps. "I—"
"Sorry," Ash says quickly. "Forget it."
It's silent for a moment.
"I won't get you a gift if you don't want me to," Eiji whispers. "I just ... I guess I just wanted you to know that I care. And—your birthday is August 12th, by the way. It was on your paperwork for the penitentiary."
Ash breathes out a laugh. "That's one way for you to find out," he says. "And the gift thing—I don't care, Eiji. It's whatever. I don't need a gift to know that you care. I just ..." He trails off.
"It has a bad association for you," Eiji finishes.
"Normally if I'm the center of attention at a party, it's"—he cuts off, laughing darkly—"not good," he finishes.
"Do you want to change that?" Eiji asks carefully.
Ash slides his eyes over to Eiji, then away. "Forget it," he whispers. "You don't need to get me anything, Eiji. I already know you care."
But you don't, Eiji wants to say. Not when Ash suggested that Eiji ... that Eiji take the opportunity to fuck him while he's still underage. He doesn't know that Eiji cares.
That settles it, then. Eiji Okumura will absolutely get a present for Ash Lynx, now and every year after.
Sighing, Eiji stands. "I'm headed back to the room," he says quietly. "Get some sleep when you can, okay?"
Ash doesn't respond, and Eiji glances at him one more time before he's out of sight.
When Eiji gets back to their room, he shakes Shorter awake again.
"What the fuck!" Shorter complains, but Eiji ignores him.
"How long has Ash had those red shoes?" he asks. "Would he want a new pair?"
Shorter's eyes light up.
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