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The objective of this study was to explore the associations between food waste and the diet quality of foods purchased and with grocery purchasing behaviors. This was a cross-sectional study among 109 primary household food providers conducting primary shopping. Participants were recruited outside of local grocery stores and were asked to complete a survey assessing amounts of avoidable food waste and grocery purchasing behaviors. The diet quality of the foods purchased was assessed from grocery receipts using the Grocery Purchase Quality Index-2016 (GPQI-2016). Variables were associated using linear regression, analysis of covariance, and point biserial correlations. We found that fresh fruits (63%) and leafy greens (70%) were the foods that were the most wasted. The GPQI-2016 total score was significantly inversely associated with the total amount of food wasted (β = −0.63; 95% CI: −1.14,−0.12) after adjusting for important confounders. The reason “food past the date printed on the package” was directly correlated with food wasted (r = 0.40; p < 0.01) but inversely correlated with GPQI-2016 score (r = −0.21; p = 0.04). Food wasted, but not the GPQI-2016 score, was significantly higher among those who grocery shop 2–4 times per week compared to 1 time every 1–2 weeks (p = 0.02). In conclusion, food waste is inversely associated with diet quality and directly associated with grocery purchasing frequency.