Fantastic, you have been using Book Like A Boss and taken a few bookings!
Now, you want to connect and sync it with either your personal and/or work calendar so that everything is beautifully synced with one another.
Once you have synced your calendar, let's take Gmail for example, the bookings that exist on your orders page will NOT be sent to Gmail for syncing. Only future bookings made in Book Like A Boss from that date forward will be sent to your Gmail calendar that you have connected.
I hope that answers your question and if you have any others, please use the chat button on the bottom right of your screen to ask me another!