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Two strings?? This is a little worrying! But fear not, since this seems like a story that's bound to have a happy ending — our crybaby seme will probably still end up with Kihoon anyways (doesn't seem like he could go too long w/o him anyways).
In between the very hot smut going on, it seems like there's a past lives kinda plot going on...Young Master Yeon—either married or engaged to the lovely lady whose name I can't recall—was likely in love with Servant Kihoon. Obviously, their love was either in secret, one-sided, and likely went unknown. (The unlucky curse also falls somewhere within here, I'm just not sure exactly where...)
Now, this is just my thoughts: the red string doesn't necessarily dictate who you're gonna spend your life with. Like, what if the person you're "destined to be with" has a long-term partner and a happy relationship? What are you gonna do? Not move on with life?? You know, Kihoon prolly didn't in his past life, either, but alas...
But I mean, Yeon has two strings, right?? And because of this, miscommunication is likely to occur between our main two. Somehow, one of the two (Kihoon) is going to get wind of this info and shut down again...
But back to the past lives thing: he probably chose the young miss back then—whether it was due to the pressures from family and society of that time, or even Kihoon's own push (how he is currently or his untimely death). And now, he's going to be forced to choose again (not that it's a hard choice—the variable he has to fight against is Kihoon's emotions).
Point is, he couldn't have Kihoon in that life, so maybe he could in the next. Something like: "If we're reborn, I wanna be tied to you in the next life." Maybe (and very likely) it was Kihoon himself who wished for it. His lack of luck could've also stemmed from the very event that would've caused the prior sentiment. Must've been unlucky to have been born not just a man, but also a servant, in that era. Could've sneaked around, but that would probably erode Kihoon's conscience.
But then all the above plus the app??? Kihoon's prolly going to be a selfless fuck again and not try to get in the way of "fate", again! Dawg, fuck fate, and fuck Yeon instead! You're in the modern era!!! Girly also looks like she'd understand too! Again, your love life doesn't have to be dictated by some strings! Fuck the strings and love who you want!!
Tl;dr: My theory is that the red string likely represents relations with persons he might have had romantically in his (Yeon's) past life, and the fact that he likely has to choose again, but his choice might be hampered by Kihoon's own anxiety.
Damn, I really can't help but yap... I hope I got their names correct...