I regret my shyness in my youth. I know the admin has given a new order, but I would like to say something about my teenage years. I remember how a classmate I liked wanted to have a first time with me and once believe it or not she pretended to be pregnant with me. You know, the kind of erotic fun where she pretended to, for example, massage her belly ect. Unfortunately, my shyness then reached its zenith. And I ended up losing my virginity to a prostitute in college. At least it was comforting enough to know that the hooker had the dimensions for my tastes. Big boobs and thicc as hell.

Losing a friendship with someone 13 years ago who I was very close to. We shared so much when were close friends, including when she became a mother. She was so good to me. But I fucked up my friendship with her with my stupid behaviour and we haven't been friends since. I miss her so much.

I'm quite a shy, reserved person in real life. I wouldn't quite go far enough to say I was introverted, but probably not that far off. It dates right back to childhood and whilst it wasn't all that noticeable back then, it become quite apparent by my teenage years that I wasn't really any good at making new friends and felt a large amount of people around me were notably 'extroverted' in direct comparison. Perhaps I should have ignored my fears and really pushed myself just that little bit further... Who knows... Maybe I'd have more friends? Maybe I'd have experienced an early relationship like most do in their late teens - which I never did... I'll admit that it's something that still bothers me to this day, some 20 years later. I suspect it always will. 

Following on from the above, for a number of years I did regret how myself and my former best friend went our separate ways back in around 2005ish. It was another ten years before we saw each other again (although we did have some brief interactions online) and that was only purely by chance. We did stay in some semblance of touch for around two years following that but sadly it wasn't to last. The reason why we went our separate ways in the first place was still quite apparent and sadly his attitude since that time had only deteriorated. I did have 'alarm bells' ringing in my head on that first 'face-to-face' contact with him in a decade but I decided to ignore them and sadly on this occasion, it eventually backfired and I should have trusted my 'gut instinct' to just leave it at that chance encounter and walk away from it. So, in the end our original 'break up' in 2005 was indeed regretful, but I'm kicking myself over perusing him a decade later to try and 'make up' for not socially pushing myself in my younger years. Sometimes the past is best left in the past...and I certainly will not ever try to contact him again (and haven't heard from him at all in any way shape or form for at least four years - I've blocked him in every way I realistically can).

I started dating my first serious girlfriend right before we both went off to different colleges. Long-distance relationships are unlikely to last, but that didn't stop her from pursuing me aggressively, nor did it stop us from trying. We became partners and best friends, puzzle pieces that fit together perfectly. I would've married her, and I thought she would have married me too: she was the smart one, and actually used to joke that she could work while I stayed home (presumably with our future kids, although this was never specifically said). She would also practice saying her first name with my last name, as if she were preparing for it. I had almost convinced myself that it was going to work out. Turns out I tragically misread the situation: while I never proposed to her, I did tell her I loved her, but she did not feel the same way. She broke off both our dating relationship and our friendship not long after. It was devastating, but I did eventually move on romantically, and met my now-wife with whom I am truly happy. But over the last 20+ years I've tried and failed to truly reach a sense of closure regarding my friendship with this person who is still very much a part of me to this day, as if my heart were a mine and she's encased in amber somewhere in there.

She died of cancer 12 years ago which, lemme tell ya, didn't work wonders for the whole "closure" thing. I think about her every goddamn day.

(March 25, 2023, 2:24 am)doubleintegral I started dating my first serious girlfriend right before we both went off to different colleges.  Long-distance relationships are unlikely to last, but that didn't stop her from pursuing me aggressively, nor did it stop us from trying.  We became partners and best friends, puzzle pieces that fit together perfectly.  I would've married her, and I thought she would have married me too: she was the smart one, and actually used to joke that she could work while I stayed home (presumably with our future kids, although this was never specifically said).  She would also practice saying her first name with my last name, as if she were preparing for it.  I had almost convinced myself that it was going to work out.  Turns out I tragically misread the situation: while I never proposed to her, I did tell her I loved her, but she did not feel the same way.  She broke off both our dating relationship and our friendship not long after.  It was devastating, but I did eventually move on romantically, and met my now-wife with whom I am truly happy.  But over the last 20+ years I've tried and failed to truly reach a sense of closure regarding my friendship with this person who is still very much a part of me to this day, as if my heart were a mine and she's encased in amber somewhere in there.

She died of cancer 12 years ago which, lemme tell ya, didn't work wonders for the whole "closure" thing.  I think about her every goddamn day.

Man, I felt sad reading that. Virtual hugs