A server having one or more processors and memory receives a plurality of messages organized as conversations associated with a user. The server receives, from a client, a request for a selected conversation that is associated with a first message, a second message that was sent after the first message and a plurality of interstitial messages that were sent at times between when the first message was sent and when the second message was sent. The server sends, to the client, display information for displaying content of the selected conversation that includes a representation of the second message in an expanded mode, a representation of the first message in a first compacted mode and a representation of the plurality of interstitial messages in a second compacted mode that is different from the first compacted mode.