I don’t know if this one counts, but the worst feeling ever was a few years ago I just broke up with my GF and this girl I worked for confessed she had a crush on me for while, so that night she invited me to her apartment.
We were watching TV, having wine and then started kissing, then things got hot, we moved to her room, grabbed a condom.
Beat in mind that it had been like 3 weeks since I had sex. It was actually an amazing time and I felt like I released like a gallon of love juice, I pull out and see the condom completely broken.
Words can not describe the fear and anxiety I got, I felt sick. I asked her if she was on the pill and she told me she quit like a couple of weeks ago, then came the most excruciating month of my life.
In the end, she didn’t get pregnant, but I aged like 10 years on a single month.