Research and theory suggest that men, on average, are inhibited from expressing vulnerable emotions such as love, whereas women do so more readily. Based on theories of gender socialization and social media uses and gratifications, we conducted a content analysis of gender differences in the domain of wedding and other relationship anniversary greetings delivered on Twitter (N = 414 tweets). We tested for gender as well as age differences in three areas: symbolic (emoji), photographic, and verbal content. As hypothesized, women were more likely to use emojis than were men. Most tweeters who included photographs in their greetings used photos of themselves and their partners today, although some subgroups of men and women preferred photos from their weddings. Age-related differences were clear: young-adult tweeters preferred symbolic emojis to deliver their anniversary greetings, whereas older/middle-aged adults opted for verbal/textual communication, particularly in the areas of tribute and inspirational statements and humor. Results are discussed in terms of gender-role socialization, social and cultural norms, and modes of communication (e.g., written letters and notes, smartphone texts) during different historical eras.