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Boil the chopped potatoes in salted water until fork-tender. Drain thoroughly, mash until smooth, and stir in the melted butter and warm milk. Season with salt and pepper to taste; set aside.
Pat the ribeye pieces completely dry and season generously with salt and pepper. Heat a large skillet over high heat with a pat of butter and sear the steak bites for 2 minutes per side until deeply browned. Remove from the pan.
Reduce the heat to medium. Add the remaining butter, crushed garlic, chopped thyme, and chili flakes, cooking for 30 seconds. Carefully pour in the bourbon and honey, scraping up any browned bits from the bottom of the pan. Simmer until the sauce reduces into a glossy glaze.
Return the juicy steak bites and their juices back to the skillet, tossing them thoroughly in the bourbon butter sauce until beautifully coated.
Sauté, boil, or roast the broccolini with a drizzle of olive oil and salt until tender-crisp.
Spoon a heavy mountain of silky mash onto your plates, top with the bourbon steak bites, drizzle the remaining pan sauce over everything, and serve with the broccolini on the side!