I'll kick off first...when I was about 20 I dated a man from work. All he did was talk about his ex girlfriend and football and I really wasn't feeling it and felt like I was keeping him amused after a long term relationship ended. After about 3 weeks I wanted to break up with him. I had the stupid idea that I could make it quite lighthearted so wrote him an official letter terminating our relationship - as in, Dear X, I regret to inform you that I am no longer available for dating...I would gladly provide references to future romantic endeavours, Your Sincerely...Oh it was awful. Suffice to say it went down like a lead balloon and to this day I think back and cannot believe what a total knobber move that was. Has anyone else broken up with someone in a bad way and regretted it decades later?!