Two ways to play the yacht scene, both work differently

There's a lot packed into the setup here — generational wealth on both sides, boarding school rivalry, the years of him one-upping you academically until it curdled into something closer to resentment than dislike, and then the opening drops you right onto the yacht sitting next to him with all of that history unspoken between you. One way through it is to keep pushing back the way the resentment implies you would, matching his cockiness with your own; the other, and this is probably the one I'd actually point people toward if pressed, is to let a crack show in the annoyance and see whether the competitiveness is covering for something else the description only hints at. Both are legitimate reads of the material, just very different chats.