Weather is closely related to consumer’s daily life. Are users supposed to tip more in the live streaming on sunny days or rainy days? Based on the entertainment lives treaming data on the online livestreaming service platform, this study explores the effect of different weather factors on users’ livestreaming tipping behaviors, and analyzes the moderating effects of live streamer experience and weekends on the relationship between them. The results illustrate that, (1) compared with cloudy days, rainy days have a stronger influence on users’ live tipping behaviors, while sunny days have a weaker influence; (2)the more experienced live streamers are, the stronger the positive effect of rainy weather on tip amounts; (3) on midweek working days, rainy days have a stronger positive influence on tip amounts. Moreover, this research reveals the mediating effect of emotional regulation on the relationship between weather factors and tipping willingness by conducting online experiments. This paper studies the relationship between the environmental characteristics of weather and users’ live tipping and its boundary conditions in the field of marketing. This research enriches the theory of related literature, and extends the application of emotion regulation theory. The conclusions also provide guidance for marketing practitioners and policy makers in the live streaming industry.