Gina Rodriguez as Jane and Brett Dier as Michael in the popular TV series Jane the Virgin, in which a shared online calendar was a plot point. Tyler Golden/© 2016 The CW Network, LLC. hide caption toggle caption Tyler Golden/© 2016 The CW Network, LLC. All Tech Considered In Sync: Is Sharing Your Online Calendar A Relationship Milestone? March 19, 2016 Like a first date, sharing a calendar can be a big milestone in a relationship. Some say it makes coordinating complicated lives easier; others think it's weird to keep such close track of each other.