People care and worry about how online and online/offline interactions should practically happen. They experiment with different tools and different visions of themselves in different situations, be they online or offline or across both. However, they feel there is no established etiquette about how purely online relationships should be conducted, but also how to transform relationships that began ‘online only’ into their social environments that reach beyond the Web. In this paper, I illustrate how user expectations of the desired practical experience conflict with the predominant model, “concentric circles of social distance,” that underlies most tools/services. Through six strategies of user workarounds I show glimpses of models that users do employ as they struggle to find stable ground for moral and ethical behavior as they experiment with interactions online.