Over the past few decades, new media technologies such as smartphones, tablets and other devices have changed storytelling and the ways stories were once delivered. Due to the shift in new media, there are new ways stories are shared through social media sites such as Facebook (an online social networking), Twitter (an online social networking service that enables users to send and read short 140-character messages called “tweets”), Instagram (is an online mobile photo-sharing, video-sharing and social networking service that enables its users to take pictures and videos, and share them on a variety of social networking platforms) and blogs (a discussion or informational site published on the World Wide Web consisting of discrete entries (“posts”) typically displayed in reverse chronological order). A popular site that uses storytelling and visual rhetoric through various social media platform is Humans of New York, a photo blog by Brandon Stanton. The photoblog introduces viewers to various stories that explore issues such a sexism, freedom and loss just to name a few and in doing so has vastly changed storytelling. The photo blog shares unique stories via Facebook, Twitter, Instagram and their site which affords viewers and user of those online communities a chance to connect and engage. Often times many of these stories receive over 1,000,000 views and are broadcasted on local news station. In an effort to understand how the stories mediated through Humans of New York become successful and afford users a chance to engage, I will analyze how the stories become successful and assess their best practices. By determining their best practices, I will use their best practices to produce three images on the subject matter loss and populate these images via my personal pages on Facebook, Twitter, Instagram and personal blog Black Attire Aficionado and monitor user engagements with the subject. The quantification of user engagement will entail monitoring the sites and record and analyze the different ways users interacted with the image. Essentially, by using their best practices, I believe I can produce user engagement to Humans of New York but on a smaller magnitude. Finally, by understanding user engagement on different social media sites, one can tailor the message for a specific audience which can contribute to a more successful story delivery.