Childhood jealousy has typically been examined in a limited number of jealousy-evoking contexts and mainly with the mother only, thus providing a narrow view on the manifestations of jealousy. The aim of the present article is to examine childhood jealousy within parent–child dyads and (mother–father–child) triads and across multiple contexts. The sample included 87 Dutch families with a toddler (38 girls, 49 boys, Mage: 23 months). Children were challenged in several jealousy-evoking situations using social and non-social objects as rivals during videotaped family play sessions. Children's jealous behavior (e.g., negativity, distraction) and jealous emotions (e.g., anger) were coded. We found the most jealous behavior in contexts including a doll as a rival and the least in the non-social object conditions. Children showed more jealous behavior toward mothers than fathers. Children showed elevated levels of anger in most jealousy situations.