It is very difficult to tell what you are trying to accomplish, so it is hard to know if this will be helpful or not (if not, please clarify your question)...
Iterate through the second set of checkboxes and see if their strings are in the list of strings from the listbox and if they are checked:
bool result1 = listBox1.Items.Contains(checkBox1.Text) && checkBox1.Checked;
bool result2 = listBox1.Items.Contains(checkBox2.Text) && checkBox2.Checked;
Then, use some
if
statements to take all the results and determine what message to display (see answer from Henry Minute for displaying message).