Dating sites have become the app du jour in recent years, now that we often meet and connect with each other online first. However, the common complaint is that most of these sites are dehumanizing, as if people were simply units of data. At the same time, harassment of women from notorious sources like 4Chan, the less than 17% of women in tech companies, and the even fewer women as CEOs all underscore the dearth of women’s agency and and voice in the digital space, a problem that negatively affects everyone. Siren, a homegrown start up founded by a female artist, has burst onto the scene in its first two months of public beta in Seattle, an unexpected antidote coming from unexpected places. As the artist, I began with the question: “How do we make strangers less strange?”and I’ll show how I went from just speaking the idea of Siren into existence, to our present model. I’ll delineate the two pain points in the online dynamic: Women’s discomfort in all current models (which also creates frustration for men) and the static data model ultimately unhelpful in finding chemistry. I will describe how Siren creatively cut through the noise of new competitors and threatens older models, so that Siren is now considered a first mover (as one of the best online dating sites already). I’ll show the Siren’s features as parallels to real life as interpreted through the lens of the artist, in which women always control the visibility of their profiles, sending clearer signals to men. I will also demonstrate how we have radically changed the way people discover others through Questions of the Day, which provides fresh, dynamically-updated user content within a conversational “water-cooler” space for users to gently find unexpected chemistry through hints of personalities. The interstitial moments of our daily lives are increasingly connected to others; Siren attempts to take the best of technology to augment human relationships in ways that make us smile; perhaps our tagline says it all: Charm Someone’s Pants Off.