What Is The Most Bittersweet Situation You’ve Experienced?

There are always bittersweet moments in life. A Reddit user asked ‘People of Reddit, what is the most bittersweet situation you’ve experienced?’ and here are 35 of the responses.



Adopting a decrepit senior dog with one hot mess of a body. He was cherished and adored by myself and daughter. My daughter was his main squeeze. He had health problems galore but he always persevered, and for a brief moment he got to BE a dog.

One year ago we helped him cross the rainbow bridge. My daughter made the decision that she would be there, she held his snout in her hands and kissed him the entire time. She was so brave, because of him.



Sitting in the hospital room, mom was about ready to pass away from cancer, everything was shutting down internally. The date was my parents’ 40th wedding anniversary. The last thing dad said to her was ‘Thank you for 40 wonderful years.’



Recently had one last sleepover with my childhood friend before he passed from leukemia. It was just like being kids again.

He couldn’t do much at the point he’d reached, but we listened to music, watched Luca (which he hadn’t yet seen), and just talked about life. And of course we stayed up way past bedtime haha



Waking up from a suicide attempt.

Bitter because I woke up, sweet because I woke up.



I always looked back so longingly on my first love. It was the summer we both turned 18 and it was my first time falling in love and everything seemed magic. She was a lifeguard and I still remember her long legs splayed over the lifeguard chair, her long blonde hair, her tan skin, her movie star sun glasses. On that lifeguard stand up high she was a shrine to everything summer. And I freaking loved summer. I had a manual labor job putting in swimming pools, damn that was so hot down there laying plaster with that Kansas City humidity.

We fell in love that summer and did everything together, every waking hour we could we spent together. In the day we would go down to the creek together and wade in the water and swim and lay on the shore, she always wanted to ride on my back across the creek to get to the other side, our side, where no one ever went but us. Sometimes we would climb on those oversized hay bales by my house and stare up into that cloudless summer sky and talk about what the future would be and going off to college and running track and the Olympics and how we would always love each other.

My favorite days though, God damnit I loved these days so much was when it rained. We both got off work when it rained so I would get an early call from my boss canceling my work and I would just lay there and smile and look at the ceiling and wait for my phone to ring, it was always her telling me to come over and we could spend the day together. Movies or the mall sometimes but usually we would climb over the gate to the swimming beach and go swim in the lake and feel the warm rain and dive under the water and come up over the dock. Best times of my life.

I’ve always looked back on them so longingly.I’ve been in love since and been married and divorced and dating but it seems my thoughts always came back to her. Even though we live in the same city it was 15 years since I had seen her. Back when I got married to someone else I had an outdoor wedding and even from the front I could hear her sobbing when I said the vows that I wanted to grow old with my wife, that was from a movie my first love and I used to watch together sometimes when it rained. She left right after the wedding and I hadn’t seen her again for 15 years. I longed to see her, I even contacted her one time and suggested meeting up but she said she was happily married and would never meet up with me, even to just talk and reminisce. I longed to see her again just one more time.

Well it happened, I saw her again for the first time in 15 years. We were both at a U2 concert and we hugged and laughed and even danced when they played With or Without You. That night we all had a great time and we walked the women all the way to their car before going to ours. I realized when I saw her Honda minivan and sippy cups from her kids and saw her face that had gotten older that I didn’t long for her. Don’t get me wrong, she was still beautiful, incredibly beautiful. But she wasn’t the girl on top of the lifeguard stand anymore. She had gone on with her life and had kids and drove a sensible minivan and wore sensible mom shoes. And then I realized I didn’t long for her at all. What I had a longing for was me. When I was 18 and athletic and handsome, with my whole life ahead of me, that was what I longed for more than anything. A life before mortgages and bills and small backyards in the suburbs with fences, I longed for that part of me that was still back there with her at the creek. What it was like to fall in love and swim under the dock in the rain and laugh and hear the words I love you for the first time. I didn’t miss her at all. I missed me. It was the most bittersweet realization of my life.



About ten years ago just before she died of lung cancer, my mom called me by my childhood nickname, told me she loved me and then fell asleep. That was the last thing she ever said to me. I was 35 when she died and she hadn’t called me that nickname in maybe 30 years. I still tear up thinking about it.



My fiance’s funeral. It was literally the first time I got to meet his mom. And she was such a sweet lady. When I tried to give her back my ring because it had belonged to her mother. She refused to take it, she told me “My son chose you to give it to. And it would be rude of me to take back his choice.” She probably still has no idea how much it meant to me.

I literally have no pictures or anything of him. But I still have my memories and my ring I keep in my jewelry box.


My family got a puppy when I was about 5. My freshman year of college he had to be put down. Every part of his body was failing. He couldn’t stand on his own, fur falling out, infections that wouldn’t go away, etc. and the vets couldn’t help him no matter what they did. My mother finally made the choice to let him go peacefully rather than try to force any more treatments and hope they ease it. I opted to be the person to go back with him when the time came.

I held him and cried. But I pet him behind the ears the way he always liked and made sure he knew he had one of his humans there. There was relief in his eyes when he went. Like he understood what was happening and was okay with it. Finally able to rest.

I didn’t want to let my childhood pet go. But I’m glad he didn’t have to keep suffering and he didn’t have to go out alone.




Oh man. I’m always a sucker for the long love.

Amidst a loooong illness in hospice and dementia that meant he recognized no one my Grampie still lit up every day when my Grammie showed up. He would turn to whoever else was in the room and say “ah, I’m just the luckiest fella in the world to have the most beautiful woman in the world to love. I love you, Dolly.”

She got to be there when he passed away and she died a few months later. I think she was just waiting for him to go first.



My friend and his fiance wanted a baby and were doing IVF treatment and were down to their last chance. She got pregnant but my friend died three months in from a sudden heart attack.

So basically super bitter for six months but then his daughter was born and is healthy and beautiful.