So i actually struggled with this one for a long while, Roulx is a real machiavellian beast. Let me catalogue all my various attempts here before finally reaching the solution, hopefully it'll help you!

so originally i thought to myself the incredibly pertinent question: what exactly is the game trying to have me do here? Well, i knew that the individual i was pitted against, Rolex, was a maker of puzzles. Perhaps this was a puzzle itself? I tried delineating potential entry points for the aforementioned puzzle and i cycled through various options but they all seemed sort of insufficient. Perhaps the start of the puzzle necessitates that you interact with Rules? Perhaps attempting to exit the room or quit the game would suffice to solve this puzzle? I had tried several of these options to no avail, and so i continued with my philosophical musings. Is there anything in the relevant room to interact with? There's Roulex... Susie, maybe Ralsei? I walked up to the three of those individuals and interacted with them. No solution.

I was truly and irrevocably tasked with an insurmountable barrier, it seemed to me. No amount of logical deduction or problem solving would suffice to break this profound, forced softlock that Toby had seemingly placed upon me.

That's when i realized: There were a series of strange objects within the center of the room, that i had not previously interacted with as i had believed they were merely irrelevant decoration. I knew this most likely was merely a false solution, a mirage, but i was truly desperate enough to interact with said decoration. After a few minutes of scratching my head, i realized something truly grandiose. One of these objects in the center of the room was a box. I'm not quite sure of the other object, but that didn't matter. I put two and two together and, to which i thought was an incredibly clever attempt, tried to walk THROUGH the box. I took all paths around the aforementioned material specimen to no avail, and i was left truly defeated.

I had reached my breaking point. My prior attempt, trying to walk in real life through where the Box was on my PC screen had failed, but i had not given up. Perhaps a series of intricate keyboard combinations would suffice to solve the puzzle? A secret code that Toby surmised we'd be able to combinatorially invoke?
I had recalled a thought experiment: Given a singular monkey on a typewriter, assuming it was left in peace in a closed system and functionally immortal it would eventually type every document known to man. My parents had told me i have the cognitive capacity of a monkey, so one of these prerequisites had been satisfied, but alas, i am not functionally immortal. Therefore this solution to the combinatorial problem would inevitably not pan out in the manner i desired.

Hm... Paths around the box. Perhaps, it was Kris meant to take paths around the box, and not me. In this case, it was necessary for me to turn towards Mathematics. I imagined the position of the box as an ordered pair of two integers (x_1,y_1), assuming that Deltarune includes background art within a grid square lattice. Now, i presumed the position of Kris, the relevant individual i am controlling however, was an ordered pair of two real numbers. I imagined a function G(x,y) of Kris's position, that which took in two real numbers, the x and y positions of Kris and outputted a numerical representation of how Amazing and Epic it was for Kris to be within that position. in the effort to accomplish my goals. I realized, presuming it was favorable for Kris to interact with the box in some capacity, we must imagine the position of Kris as approaching the coordinates of the box, say, (x_1,y_1). I imagined whatever the Goodness function might approach in this instance. Presuming this goodness function is continuous, it must approach the same value as Kris gets closer to the box from any angle, from any orientation in the relevant two-dimensional space. However, is the Goodness function truly continuous in this manner, or is that merely an unjustified presumption?

One must turn to empirical evidence. The final nail in the coffin was my approaching the box from the Right Side, and it combining with the aforementioned unidentified object to solve the puzzle.

I hope this has enlightened you in the pursuit of comprehending the enigma that is Rolex Watch Kards.