Risk‐neutral sellers can extract high profits from risk‐loving buyers using lotteries. To limit risk‐taking, gambling is heavily regulated in most countries. In this article, I show that protecting risk‐loving buyers is essentially impossible. Even if sellers are restricted from using mechanisms that resemble lotteries, they can still construct selling mechanisms that ensure unbounded profits as long as buyers are risk‐loving, at least asymptotically. Asymptotically risk‐loving preferences are both sufficient and necessary for unbounded profits. Buyers are asymptotically risk‐loving, for example, when they are globally risk‐loving, when they have cumulative prospect theory preferences, or when their utility is bounded from below.