Oh Deer
First date, dinner with a girl I really liked. When leaving, I back my car into another persons car. Embarrassed, but I handle the situation, exchange info, etc. While driving her home, I hit a deer. I got out of the car to evaluate the damage and discover that the deer is alive and suffering.
No animal control to euthanize, so I did the humane thing and ended its suffering (in a quick and respectful manner). Awkwardness ensues. We never had a second date. Story credit: Reddit / dinnertainment