Like the post I had before on "How to use multiple fingers on iOS's Touch ID?", I am going to be posting some "How to" articles on this site. These are not your regular "How to" articles but are solutions to common but surprisingly complex roadblocks you might encounter while using Apple products. Some of these like this post had even me perplexed. Thanks to a friend of mine, I did not have to Google this topic to find out the answer. Ok let me dive in to the topic.
Apple's iMessage has revolutionized personal messaging service. It predates WhatsApp and other now popular mobile messaging clients in terms of being omnipresent and it should boast one of the largest subscriber bases. It has had its share of issues since its inception but Apple has made steady progress in iMessage stability and most recently with new features on iOS 10. But there are always edge cases and recently I found myself in one. I had sent someone a confidential number as an iMessage and I know that it goes into the cloud right after I hit "Send" and cannot be deleted permanently. But I did not at least want it to prominently displayed on my iMessage window every time I click on that person in the future, in case some prying eyes spy on my iPhone without my knowledge. So simple right, just delete that one iMessage, so that it at least does not display the confidential message blatantly on the screen.
But look at the image on the left (I just chose a generic iMessage conversation for demo purposes by the way). There is no straightforward option to delete or select an iMessage in that screen. You can click on the "Details" option and the screen on the right appears, but even hear there is no way to select individual or groups of iMessages to delete or do something else with them. So how do you delete an iMessage? You need to long press on any one iMessage and more options pop up, like the image shown to the left below. But even then the option we are looking for does not exist. Then you realize that there might be more options in the "More..." panel, though there is no indication of what there might be in that option.
But once you click on the "More..." button, then suddenly the iMessage you long pressed on, in the beginning has a selected arrow to the left and now you can select individual and group iMessages and then hit the trash can button the bottom left of the page to delete them. Wow... talk about number of clicks to delete an iMessage! Here you can also "Delete All" the iMessages in that conversation or as shown in the figure to the left below, you can forward an iMessage to someone else.
Now, we need to understand that deleting an iMessage is not a need most of the people find themselves having most of the times and it makes sense for iOS to prioritize this option the lowest. This is one of the perils of building an operating system that is as intuitive and straightforward to use as iOS. Sometimes certain edge cases find themselves in such awkward UI destinations. But as long as its an edge case it should not be a big deal. But I was amazed that myself a guy who has been following Apple for a long time and someone who has had almost all the generations of the iPhone and iOS could not figure out a seemingly simple task like "How to delete an iMessage" on iOS! It goes to show that what you know is only a handful while what you don't know is an ocean full...