The 2019 edition of the World Congress of Families (WCF), held in Verona (Italy) from the 29th to the 31st of March, marked a turning point in the contentious interplay between, on the one hand, pro-family and anti-gender movements and, on the other, the latest wave of transfeminist mobilizations. Not only the physical urban space hosted opposite demonstrations, with the pro-family and anti-gender groups organizing a “March for the Family” at the end of the Congress and the transfeminist movement “Non Una Di Meno (NUDM)” holding a three-days set of events that culminated with a march and a national assembly of the movement. During the WCF, social media provided a further space wherein the conflict between conservative and transfeminist visions of gender relations unfolded and enriched through the continuous production and circulation of user-generated content. Leaning on social movement studies and endorsing a vision of the digital space as a space of contention, this paper aims at analyzing the interplay of clashing representations of gender issues – particularly, reproductive rights, parenting issues, sexuality, equality between all gender subjectivities – as part of a movement-countermovement dynamic. More specifically, the paper analyzes a composite dataset gathering all tweets and Instagram posts published publicly during the WCF period and, by employing Google Visual API and Semantic Network Analysis, isolates and scrutinizes the main images/meme/hashtag that traveled with the official hashtags of the Congress. Results of our analysis suggest that both sides systematically employed images/meme/hashtag to support their visions of gender relations yet in the context of different tactics. While pro-family and anti-gender groups tend to use images/meme/hashtag to provide evidence and substance to their claims (e.g., the happiness and righteousness of the “natural” family), NUDM bends images/meme/hashtag towards irony to counteract and expose to ridicule their opponents.