What Is The Most Bittersweet Situation You’ve Experienced?



Unintentional pregnancy the month after a miscarriage.

The pregnancy I’d lost had been planned, wanted, and tried for. The baby had a name and a place in the family I was building for myself. The miscarriage was physically traumatic, required surgical intervention, and had me seriously questioning if I ever wanted to be pregnant again if I risked that happening a second time. I had just decided that I couldn’t face the thought of another pregnancy. And then I missed my period.

I got medical bills from my current pregnancy that said “prenatal care” and bills from my surgical procedure that said “incomplete abortion.” I missed one of them somehow and got a call from a debt collector about it shortly after the second baby reached viability. (24 weeks of pregnancy, at which point the baby has 50/50 odds of surviving premature delivery.) My original due date passed and I was pregnant with someone else. And I couldn’t get drunk about it, or even just lay in bed not eating or showering, because I was pregnant with someone else.

The second baby is a healthy toddler and is currently watching his big brother play video games. He is very loved. Carrying him scared the absolute s**t out of me.



Watching my babies grow. Obviously I want them to grow well but if I could just pause time for a bit.



At my grandmas viewing my little cousin (2)and her dad (my uncle) walked up to see her and to say their goodbyes. As they walked away my little cousin turned to her and waved goodbye


A friend’s step father had been thru a nasty divorce ~20 years back at the time. Was told his disabled daughter died in a car accident. His daughter was told he died in a car accident.

Daughter never stopped looking for him but he was a very tin foil hat kinda man. Didn’t work anything that wasn’t under the table, Didn’t own anything that could be tracked, whole nine.

He had a fall one night and got very sick. Decided to marry his long time girlfriend for the health insurance.. court house wedding, straight to the hospital. He was hours away from death, was put into a medical coma and admitted to ICU. Lots of touch and go. Needed major heart surgery and some other unattended health issues caused complications.

I was living him and his new wife at the time. Wife was with him at the hospital when his daughter showed up at the door. She found him through the marriage certificate. I had to pull her caregiver aside and tell her dad might not make it after she spent some 20 years looking for him.

He lived a few years after that so was a happy reunion for them. But they day she found him finally, just to be told he may be on his death bed. I’ll never forget that moment.



divorcing my ex. she cheated and was abusive. it was LONG overdue and any feelings were and are gone, but the old romantic side wanted to be married until the end. wanted a 50 year anniversary. so sweet in that i was able to break free and find myself, bitter because divorce sucks. remarried and i love my wife to death, but at our ages, the big number anniversaries are very unlikely




Getting the greatest job and worst boss at the same time.


Graduating from university.

I was incredibly sheltered growing up and as a consequence, I was scared of everything and would jump at my own shadow. I had my first taste of freedom at 16 and up until that point, I had never had noteworthy life experiences – no sleepovers, no going to the mall on my own, didn’t know how to cook, etc. Yes, my parents had watched me like a hawk growing up and didn’t allow me to do a lot on my own. Anyway, on to uni. I was young, tiny, wispy, shaking with anticipation at the prospect of moving out, going away and living in a university dormitory with my peers. I didn’t know anyone. I didn’t think I would make any friends but I did, and we did everything together.

I remember getting sick and missing my mom and my roommate passing me the flu medicine from her own stash. I remember trying alcohol for the first time and my friends laughing silly while a girl throws up behind the couch. I remember discovering boys for the first time and deciding they’re not as icky as I thought. I remember going on road trips, holding hands with strangers I met in a mosh pit, trading kisses and spit with the most beautiful boy only to forget his name and face the day after. My classes were interesting and the beautiful weirdos I met as I hopped and skipped through my university life were just as engaging and so I studied them just as intensely.

I remember surviving my freshman year and being drunk in my own potential. Oh, to be young and invincible! Adulthood has its own set of fun and challenges but I know that I will never be this combination of hope, innocence, curiosity and bravado ever again.




The last conversation I had with my Grandad he was reminiscing about when he was a farmer, and started talking about his horses. I asked him how you took care of a horse back then (he stopped farming in the 1950s, the conversation was in 2004) and he spent a good 30 minutes explaining what they did and how much land you needed etc. A simple conversation about country life and animals, two of his favourite things.

I live in another country so when I said farewell I had a nasty feeling it’d be the final time I ever visited or saw that house. He died 10 months later. The next time I was able to get to England was in 2011 and I visited his grave instead.



I finished University not that long ago. I was very excited because I literally went through four years of an engineering degree just for this moment and it finally happened. But the moment the graduation ceremony ended I just turned really sad. It’s over. Everything good in University life is over. Plus I’m like, an adult now? What the f**k! I don’t want that!



Realizing there was a mutual love with a friend, but that it was platonic, and we absolutely wouldn’t work as a couple


Receiving a check for my inheritance as part of Dad’s estate.



My dad crying out of happiness while wishing me a happy 15th birthday…

I couldn’t really process what I felt, because I was secretly dealing with mental health issues since the past 1-2 years and I pretty much forgot what happiness is and have been in a numb type of mood. I believe that that night was the first time I cried out of what may have been happiness.



When I was 17 or 18 I met a girl online. She lived in Florida, I lived up in New England area. We chatted all the time, got very close. We eventually met when I went down to visit my parents for spring break Senior year of college to FL. I was head over heels in love with her but the age, the distance and not having a career or money at the time really just didn’t lend itself to us giving it a shot.

She went into the army for a short time, did service got out. Met a fellow vet who became a firefighter. Had 4 beautiful daughters was really happy for her and figured she had a great life. 3 years ago the husband was cheating on her, recording a house-sitter with a hidden camera in the bathroom and other places, also cheated on this woman with said house sitter and others. Was going to be tried for the recording and for statutory rape of the others who were all under 18.

Before that happened on Halloween that 3 years ago he got drunk, beat the hell out of my friend and fled. Committed suicide.

What that poor woman went through, and the underlying guilt I feel like maybe she would have had a better life if we were together will always seem bittersweet to me.



Saying goodbye to all of my friends and my hometown to move to college. I’m excited for this new adventure but all of us chilling in my basement playing board games for the last time killed me the moment they had to leave. We were all doing just fine until then, when one after another they started crying as we hugged goodbye. I held it together. The moment they drove away I sobbed. Happened about a week and a half ago so it still hurts. I know that I have (and will) experience much more sad things but this is fresh enough that I’m still heartbroken.




Finding out my housemates suicide attempt was just a cry for help