| :-( | Direction | Horizontal (tilted 90° to the left) |
| Shortcut | AIM Instant Messenger |
|
| Rank | ★ ★ ★ Common | |
| Updated | 2007 | |
| Description: Implies the writer is sad about something. Often used to express sympathy as well. | ||
| :( | Direction | Horizontal (tilted 90° to the left) |
| Shortcut | AIM Instant Messenger Google Gmail |
|
| Rank | ★ ★ ★ Common | |
| Updated | October 30, 2009 | |
| Description: The left parenthesis is often used to represent a frown or sad expression. | ||
| :o{ | Direction | Horizontal (tilted 90° to the left) |
| Shortcut | No | |
| Rank | ★ ★ ☆ Average | |
| Updated | August 20, 2009 | |
| Description: This atypical frown emoticon can be used to express sadness or discontentment. | ||