Yeah - it’s kind of always an odd part of the show. I just kind of ignore it for the most part. I did like in S2 when they talked about “eating sandwiches” instead of smoking pot. It was a good way to deal with the topic and acknowledge the storytelling framework.
But I find a lot of the behavior on HIMYM creepy if you spend any time talking about it - Marshall’s obsession with the supernatural, Ted’s “romantic” moves that tend to fall on the side of stalker, and of course I think Robin will gun someone down in a very special episode.
So you’re totally right - it’s weird to spend time telling a story to your kids about how you landed some totally awful chick. And that it was okay to sleep with her and never talk to her again because she was awful.
Maybe sexual openness is something we can better embrace in 25 years (where the retelling is set).