Claude is pretty good at this. I finally caved and gave it access to my calendar so I could run a weekly "check what's on nearby and suggest some activities" workflow. It looked at my past calendar activities, built a "taste profile" from that, and now regularly sends me tips for stuff I might want to go to. If I'm keen for something it adds events to the calendar, and optionally invites my partner. It's also surprisingly good at finding "wildcard" events which don't necessarily closely match things I've been to before, but are often interesting to me anyway.