Some words have more than one translation across languages. Such translation-ambiguous words are harder to learn, recognize, and produce for individuals across the language learning spectrum. Past research demonstrates that learning both translations of translation-ambiguous words on consecutive trials confers an accuracy advantage relative to learning them on separate sessions. We tested the proposal that presenting the two translations of translation-ambiguous words simultaneously on the screen could facilitate the formation of a more integrated mapping, because this would enable learners to make direct comparisons between them, whether implicitly or explicitly. We predicted that this facilitation would especially hold for translation-ambiguous words with related translations. Fifty native English speakers learned 48 German words with one or two translations that varied in the meaning similarity of their translations. Paired associate training took place on a Monday, and a first language (L1) to second language (L2) translation production test took place on Wednesday and Friday. Generally, higher translation similarity facilitated translation speed. In accuracy, training condition interacted with the similarity of the translations; translation accuracy was more affected by translation similarity in the simultaneous condition and went up as similarity increased. Overall, the consecutive condition demonstrated higher accuracy and faster reaction times than the simultaneous training condition, suggesting that learners may have been unable to successfully divide their study time between multiple words on the screen without explicit instruction.