I have run with my mom in the past but because of our weird dynamic it has ended up being stressful rather than happy.

I do like to run with friends though. Even if we don't go quite the same pace, it's fun to have someone out there with me, slogging along. Plus it keeps me accountable: if I say I'm going to do 45 minutes, there's never any doubt that I'll do it if there's someone with me.