It was december 31st, around 3 am, my girlfriend, her best friend, and I just had come back from a party. The three of us were drunk but my gf was completely wasted. We took her clothes off and put her in bed. Seeing her naked laying there, she confessed to be extremely horny, and my dirty mind just started wondering about the beautiful image of those two lovely girls kissing, and the three of us. I shouldve asked, it was the perfect time, us three there, I was sober enough to know exactly what I was doing, drunk enough to actually give a flying fuck but I didnt because I was too much of a pussy.
We're no longer together, and I'll never know how that night might have turned out, all I know that whatever the outcome, today it wouldnt have mattered.
I go to this KFC/Taco Bell few blocks away from my house. Working at the drive through there was this girl with gorgeous eyes. I have seen her before, and she cared enough to actually call me sweety, shared a smile, and flirt a little. I'Ve been dying to ask for her number, but around her I would get so nerveous I never got the chance to. Took me a while to build up the courage, and when I was finally ready, she was gone, and didnt see her again. I regret not trying the very first time.
Many years ago I was friends with a coworker. She's gorgoeus, the type of girl you'd die for. We would hang out almost every day. At work being around her it was like a dream, and after work we would go out to eat, or just hang out at my house. Any time I was flirting with someone, she'd be mad jealous, and I'd be flattered. Talking on the phone, she asked "you have had so many chances with me, why would you never make a move or just kiss me?" All i remember answering was: "because I'm too shy, and intimidated by you" I regret those words every day of my life. I never got another opportunity with her, and we stopped being friends. Few years later, we're on different career paths, and even though we live really close from each other, she wont even make the time to go for coffee, I've tried, a lot! one day I dared to ask: "would you give us another chance?" Her answer was: "I dont think of you like that any more."
After my dad passed, I look back to all these experiences and all I can think of is I'm such a dumbass. When facing death like he did, none of this, rejection, a break up, the fear to lose or even be embarassed matter, all that truly matter are those opporunities that I was too scared to take, and the pain of regret is far greater than facing the unknown.