You felt like you had a good sense for people at this point.
Your talent for information gathering required you to know people, how they act, and to decipher whether they're lying or not. Some leads could turn out to be duds regardless, but for the most part, you've nailed down the art of getting what you wanted out of other people. It had also given you the ability to judge a person just on a first impression, and you liked to think you were spot on with it; the gang had a tendency to trust your judgment, since you rarely proved to be wrong.
You were also known to be too nice for your own good, even for a thief and murderer, and though you'd never go against the gang's wishes, you couldn't help but linger near the pitiful prisoner.
"Please... Just some food..." The poor thing had been tied to the tree for days now, Kieran was his name if you remembered correctly.
"Why don't you just tell us what we wanna know?" You ask innocently, though you try not to make it obvious you're talking to him. You're not sure Dutch or Arthur would be happy to see you chatting with the enemy, though you wonder if they ever considered using kindness when it came to coercing people; you doubted it. "You know we'd be more likely to spare ya."
"It'd be a death sentence."
"Being tied to a tree without food is already a death sentence, hon. You might as well give yourself a fightin' chance."
You leave him to ponder this and finish up your own chores, still feeling guilty that you couldn't give him a little something to eat but wanting him to just give up information on the O'Driscoll's. If he hated them so much, why not just give them up? If he as able-bodied, Dutch might even consider letting him stay around, as long as he makes himself useful. You would certainly try to vouch for him, especially since from your very limited interactions with him Kieran hasn't really felt like he was a bad guy.
You're pleased when not even a day later, Kieran finally relents and lets the boys in on where Colm was hiding out. You thought he was telling the truth, something you mention to Arthur off-handedly before he leaves with John and Bill to go check it out. He nods and seems to take it into consideration, but you know if anything went wonky during their ride there, Kieran was as good as dead. You made eye-contact with said hostage, who nodded nervously at you, as though thanking you for the advice you gave.
You're pleased to hear that Kieran gets to join the gang, even if there is still some heavy suspicion surrounding him; you knew he'd probably turn out to be the punching bag for some of the rowdier members around here until he really proved his worth. You were among the only people to show him kindness, even mentioning you're glad he decided to stick around with the people who tortured him for days; he chuckles at that and looks rather flustered, admitting that being among the O'Driscoll's could be much worse.
At this point he'd been with the lot of you for a few days, helping out with chores around the place and chatting with those who'd give him the time of day. You noticed he was rather kind, probably not wanting to step on toes but you sensed it wasn't too far from how he actually was. You'd only interacted with him once or twice, the first time being him thanking you for helping him get a chance (you'd openly spoken up and supported the idea of him staying with you on a preliminary basis) and the other having him help you with a rather boring chore that was made a little more fun by having someone to chat with.
"You're- You're really too nice to be in a gang." Kieran states out of the blue while you're eating dinner, thankfully not around any of the other members who might taken offense to that statement. You smile, knowing what he's getting at and reaching over to pat his hand.
"You haven't been with us long enough to see me do my worst." He stares at your hand that's now resting on top of his, shifting around nervously in his seat. "I hope you stick around long enough to figure that out, though. I kinda like you, Kieran."
Your flirtation was a bold move, and was performed more because you'd love to see how he'd react; his squirminess just because of you touching him was cute, so how would he react to being openly flirted with? For the most part he just gives you a wide-eyed look, probably wondering if he's still tied to the tree and simply hallucinating, but he finally gets it together enough to give a response.
"You, uh, flirt with every guy you take captive like this?" It's meant as a joke, not an insult, and he's once again pretty lucky that there's no others around because you're sure someone would've gotten offended on your part. But you find it funny, giggling in response and slowly removing your hand from his.
"Nah, only the cute ones." You stand, getting ready to head back to your tent. "And trust me, we don't get many of those around here. Not any that get to live to see another day, anyway. So count yourself lucky."
Kieran stares at you, as though mesmerized, before finally mumbling, "I do."