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Squid Salad with Cucumber, Watercress, and Cilantro

['1 tablespoon vegetable oil, plus more for grill', '1 pound squid (bodies and tentacles), cleaned', 'Kosher salt, freshly ground pepper', '2 tablespoons (or more) unseasoned rice vinegar', '1 tablespoon (or more) chili oil', '2 Persian cucumbers or 1 English hothouse cucumber, thinly sliced lengthwise', '1/2 bunch watercress, thick stems trimmed (about 2 cups)', '1/2 bunch cilantro', 'thick stems trimmed (about 1 cup)']

Prepare grill for medium-high heat; oil grate. Toss squid with 1 tablespoon oil in a large bowl; season with salt and pepper.
Grill squid, turning occasionally, until lightly charred and cooked through, about 4 minutes. Transfer squid to a cutting board and slice bodies into bite-size pieces.
Toss squid with vinegar and chili oil in a clean large bowl. Add cucumbers, watercress, and cilantro and toss to combine. Taste and adjust seasoning with salt, pepper, and more vinegar and chili oil, if desired.

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