Somewhere in between
I tell them as soon as I feel any potential interest with someone who is a reasonable candidate (meaning, not a woman I saw on the train but didn't talk to, necessarily, but definitely a woman with whom I felt an attraction and was considering asking out/hanging out with/meeting in a group/etc.).
I keep them up-to-date, but they don't get gory details. So, "we had dinner and a movie, and sex," yes. "We had dinner, ate sushi and I ordered the seaweed salad; we watched the latest Star Wars and she hated that everyone kept looking for Kirk and didn't care about the hundreds of thousands of people that just died; we went back to her house and did X sexual thing, Y sexual thing, and then WXZ thing that involved monkeys and chandeliers." No.