[simscitizen]

If you type the name of the person, it should allow you to create a filter for "Messages with: Person". It should also pop up a filter bubble for photos. From there I think you can type in some query and it should do a query on the photos via text. I don't think you can add your date filter though.

Second way would be to open that conversation view, click on the contact icon at the top of the view, which should then bring you to a details page that lists a bunch of metadata and settings about the conversation (e.g. participants, hide alerts, ...). One of the sections shows all photos from that conversation. Browse that until you find the one you care about.

[TheDong]

I admit I was wrong in my understanding of iMessages capabilities.

I remembered its search sucking, and also it not working on all my devices, so I quit using it and regurgitated a stale criticism.

Still, the search is useless to me if I can't do it on my linux desktop (like I can with email, discord, and every other chat service I use), so I'd still say iMessage has a laughably lacking search by nature of it only working on ios/macos, when all other chat apps I use offer at least some search on ios/android/linux