That could definitely still work! It just depends on who you’re trying it on! 
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Interesting… 
Usually my MCs are quite shy in terms of affection and they don’t usually flirt. XD
Luckily, most flirtatious options are often not required to gain affection with characters if that’s not the character you want to play as–there are always other ways to get that–and in fact, with some characters, it might even backfire and turn them off! But with others, you might miss the window/romance flags and they might assume they’re friendzoned. And some characters will be the ones to show interest first, while others need a little nudging and hinting from you. It’ll be a mishmash!
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A challenge huh? Hmmm… Must understand Blade’s behaviour…
Thank you so much for answering my questions. I hope it didn’t bother you much. 
Not at all! I just hope I’m not spoiling too much, haha!
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Oh cool, I helped!
What have I done???
Ahem…anyway. That sounds like a plan, @rinari!
I kind of expected the other Shepherds–well, ok, maybe just Blade and Tallys–to be against the idea of the MC inviting their trusty sidekick to live with them even if he probably could be used to fetch coffee so it makes sense that you’d have to be fairly well-liked for that decision to not be immediately shot down.
Would it be spoileriffic if I asked when such a decision could come up? As you said, it wouldn’t even come up unless the Equalists are dealt with, but I must admit I’ve grown so attached to Caine that the idea of him being on his own makes me antsy, lol.
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It’s great to see the mechanics so we could strategize accordingly. 
Kidding aside, I don’t think it’s spoiler-y and seeing what your thought process is would help us as your reader to provide you some feedback.
[looks at Blade]
[looks at Blade again]
(at least that’s my guess for how his romance will go, lol confusing as all get-out)
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Aw, that’s sweet that you’re protective of our trusty sidekick! 
I can’t make any concrete promises since I haven’t implemented it yet, but at the moment I’m planning on it coming up in the direct aftermath of the Equalists chapter, so it would be pretty immediate if that’s the route you were to take. 
Blade and Tallys would certainly be iffy on the idea of a rando kid joining the Shepherds, so you’d have to some pull with them–but luckily Trouble is the type who would adopt any lost puppy who came along without a second thought. That’s pretty much how Shery joined anyway, lol.
re: Blade… not exactly, but I’ll leave it a secret?.. He’s definitely an interesting one! 
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Caine is a good kid. =D If you plan to consider it, that would be great.
Blade’s character looks interesting by the minute.
You just love torturing us, dontcha? lol
Yeah, he reminds me of my little brother when he was that age (…actually he hasn’t changed much in the intervening years, except he got more sarcastic 
), so my Big Sister Instincts™ are on high-alert now that the Equalists are running around. 
Ain’t no one messing with my surrogate lil bro!
How many puppies do I give Trouble until he and I are married?
Ok, but seriously, I think Trouble may have just edged Blade out into being the RO of my first playthrough.
Sorry Blade, maybe in my third playthrough after Chase? 
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Is blade the type that when he realizes he is into you he just comes out and says it? Straight to the point? I have a feeling he wouldn’t wait to be friend zoned.
Yeahhhhh… Trouble you little… troublemaker. Stealing peoples hearts and stuff. 
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Am I missing something but have I miss meeting Chase?
Oh, no. We haven’t met him yet. I just really like thief and antihero archetypes and guess who fits 'em to a T and is also romanceable??? [waggles eyebrows]
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Hmmm… I wonder who that is…
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He’s the leader of the thieves guild and sounds like a total bad boy. So I’m interested.
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I look forward to missing every romance flag because I’m being flirty when it’s bad and not being flirty when it’s good.
and there is nothing you can do to stop me.
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What if she throws you curveballs where the character flirts with you?
I assume then it becomes a game of dodgeball? lol
miss me with that romance
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Good to see that he’s still the best boyfriend.
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all by accident of course
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