Gmail search for recipient last mail

Hello, a common use case in everyday business is to take a quick look at what I last communicated with a business partner. So I click in the Sent folder, search for the sender and then want to quickly see the last message sent to them. However, if I then click on the first search result (date), older messages also appear initially expanded. I have to tediously look in the conversation view to see what the last message was. Am I doing something wrong? I find it quite confusing to figure out the order in which the excerpts appear. It looks wildly thrown together.

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That's the nature of threaded mails (conversation view in Gmail). If you search, it will show you the last *conversation*. When you open the conversation, the last message sent will be at the top. 

The only way around this is turning off conversation view. That will sort your messages chronologically without threads.