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Good pairings are usually about contrast and balance rather than similarity. A rich dish wants something bright to cut it; a spicy one wants something cool or sweet to soften the edge. Once you can name what a dish is - fatty, acidic, sweet, bitter, spicy - you can reason your way to what it needs alongside it.
Pairings that show up again and again for a reason.
Rich pork with tart apple; fried food with a lemon wedge; creamy pasta with a bright tomato. Acid slices through fat and keeps each bite from feeling heavy.
Honey on a spicy wing, mango with chili, hot pepper in chocolate. A little sweetness rounds off the burn and makes heat moreish instead of punishing.
A fatty cheese with a crisp pickle; a heavy stew with a fresh herb on top. The bright note resets your palate so the rich part stays exciting.
Salted caramel, prosciutto and melon, cheese and honey. Salt makes sweetness taste deeper and keeps it from cloying.
A plate feels satisfying when it hits several notes at once: something rich, something bright, something with crunch, something with warmth. If a meal feels like it is missing something, run down that list - most often the gap is acid or texture, not more of the main event.