IMessage crashes, can't delate old messages

After I launch iMessage, I can't delete old messages. When I select a mesage, a dialog box appears and does nothing. Niether delete nor cancel responds. I quit the program and restart, same result.
I am using an iMac 2.4 Intel Core 2 running OX 9.2

Hi,
Could you manage to grab a Screen Shot of that ?
CMD + SHIFT + 4 and describe around the area.
It can then be posted here using the camera icon in the reply field.
I get the impression that the side bar shows several conversations or chats and that clicking on one is not being that one to the "front" or make it the focused Chat is any way.
If a dialogue box is appearing at this stage it would appear to be one I have not seen before unless you are choosing Delete from a Right click menu or the File Menu which make this one pop up.
Does the selected Chat/conversation appear in the Recent Items List ?
Can you access it from there ?
The default length of the list is 10 items set in System Preferences > General pane (along with Servers and Applications as "Documents").
If the Conversation is before this it will have been dropped from the list.
It is late where I am and it will be some time before I reply again.
10:03 pm      Tuesday; April 15, 2014
​  iMac 2.5Ghz i5 2011 (Mavericks 10.9)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 Couple of iPhones and an iPad

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