Can Both Sides of a Skype Chat Be Deleted?

There is no way for you to personally delete both sides of a Skype conversation. Furthermore, deleting the Skype conversation on your side only removes it from your Skype record: If your contact goes back and views her conversation history with you, she still sees the entire chat exactly as it took place. The only way to completely erase both sides of the chat is to do so cooperatively with your contact. If you both agree that the chat should no longer exist, you can both individually delete it.

Deleting both sides of a Skype conversation is not as simple as selecting the person with whom you wish to delete the chat, selecting the date in question and then pressing "Delete." Instead, you must delete all of your chat history -- not only for this particular contact, but for every contact you have in Skype. Depending on what it contains, getting rid of this particular conversation may not be worth deleting all of your other Skype history.

The option to delete your Skype history is located in the "IM Settings" portion of the "Options" list, found in Skype's "Tools" menu. You must opt to "Show advanced options" before you will see the relevant options. Here, you can do more than simply delete your past Skype history. You can also decide how long Skype should keep your chat history. Your options range from "No history" all the way to "Forever."

Sometimes you only need to delete individual messages rather than your entire Skype history. If you sent the regrettable messages within the past hour, you can simply delete them, which makes them vanish from both sides. Right-clicking the message in question provides you with a list of options including "Remove," which deletes the message. When you use this option, Skype displays "This message has been removed" in the space that used to contain the message. This is true on both sides of the chat; your contact sees the same notification about a removed message.