Something like 5% of the time when I pair my airpods to my apple wathc to go for a run, only one of them pairs. So, if I've actually started running, I then have to circle back to get the headphones case, unpair them, stick them back in the case and hope it then works after i close the lid for a minute.

Anyone have a solution for this?

I had that problem with PowerBeats Pro. Sadly, my solution was to get new headphones.

Well you need to bring your iPhone to take selfies for Strava anyway because otherwise the run doesn't count.