cupsell Share definition Flag Getting you to pay more for a date wif a chick wif bigger boobs than da one you'd originally been gonna go out wif. I care about da size of a gal's HEART a lot more than her titties, so don't try to cupsell me! cupsell by QuacksO November 18, 2025 0 0 Get merch Get the cupsell mug. Buy Now — $32.95 See more merch