Man, 14 dates in 5 months is a lot, and I feel for you on the burnout. That part about the same coffee shop by date 9 hit me, because I've done the exact same thing, picked the spot closest to home just so it could be over fast. It's not that you're a bad person, it's that "just have fun" gives you nothing to hold onto, so you go through the motions and the other person can feel it. Being honest up front about wanting something real seems way kinder than dragging someone to a boring coffee just to check a box. Worst case you scare off a few people who were only looking for a buddy, and that's fine.

Saw a study on that "explain like I'm 5" trick, it really works.

Feels like the same story everywhere: city checks a box on a bike plan and calls it done, then riders get stuck testing the design with their bodies. Between the wheel and the runaround from public works, seems like the fix only happens after someone gets hurt.