New health behaviors are difficult to maintain and meditation is no different. We tested two key pathways of the upward spiral theory of lifestyle change (Fredrickson, 2013), which identifies positive emotions as critical ingredients for the maintenance of new health behaviors. The present experiment combined a laboratory session that introduced novices to meditation with a 3-week follow-up period to assess the extent to which study participants maintained this new health behavior. In a 2 × 2 experimental design, midlife adults (N = 240) were randomized to (a) learn about judicious ways to prioritize positivity (labeled “prioritizing positivity plus”) or about a control topic that also featured the science of positive emotions and (b) follow a guided meditation based on either loving-kindness, which provided an opportunity to self-generate positive emotions, or mindfulness, which did not. All participants rated their emotions following the initial guided meditation and reported, week by week, whether they meditated during the ensuing 21 days. Analyses revealed that being exposed to the prioritizing positivity plus microintervention, relative to a control passage, amplified the effect of engaging in loving-kindness (vs. mindfulness) meditation on positive emotions. Additionally, the degree to which participants experienced positive emotions during first exposure to either meditation type predicted the frequency and duration at which they practiced meditation over the next 21 days. These findings show that the enjoyment of meditation can be experimentally amplified and that initial enjoyment predicts continued practice. Discussion spotlights the importance of differentiating effective and ineffective ways to pursue happiness. (PsycInfo Database Record (c) 2020 APA, all rights reserved)