I was tempted to say I've had no really bad trips…then I remember a hut trip I took about 8 years ago.
The trip was to Brainard Cabin. A rustic cabin well known to day trippers in the Boulder area during winter. Very, very, very easy to get to. It is only ~3 miles one way with minimal elevation gain.

Inside are hot drinks, an inviting fire place and a place to warm up and dry off before heading back to the car or pushing further into the wilderness for more winter fun. At only a $1 donation for a day use fee, it is rather nice.
If you are lucky, you know a Colorado Mountain Club member and can assist in hosting this cabin. You make the hot water during the day, stoke the fire, clean up a bit and lock up the cabin after the weekend.
At night? You and your friends have this place to yourself. At 10k ft or so, the winter wind is howling off the divide, the night air is cold and the snow is often coming down hard.
But inside the cabin it is cozy for you and your friends. The hot drinks (with maybe a splash of butterscotch schnapps for cocoa?) are warming and the food is often yummy.
The experience is quite nice.
So, I was invited to go along and told to bring a guest. I had been there before and looked forward to trip
I took my girlfriend at the time. Thought the trip would be a great way to introduce her to the a hut trip experience that was not overly difficult.
The girlfriend was (is) a sweet woman who I am still on good terms with. We could not be any different though. Years later, I still wonder how we ended up together? :)
Me: Blunt guy from the Northeast with a sarcastic sense of humor, outgoing and quite a few friends. Loves long intense trips. Self-taught in many ways for field (IT) of employment. Came from a rather traditional blue-collar and ethnic Catholic background. As with many people who who went to Catholic school for many years, I ended up a devout atheist. :D
Her: Sweet southern girl. Introverted. A few close friends. Very sensitive. Preferred short trips at very casual pace. Father was an academic and she was (and still is) in academia. Besides a different social and economic background, she was (is!) deep into the New Age woo-woo stuff. :)
We made an, ah, interesting couple.
So, that sets the stage.
Also, did I also mention she had NEVER been on any overnight winter trip and grew up in South Carolina????
So we get to to the trail head and its exposed paring lot. If you have ever been there, you know that the Brainard Parking lot is by far the worse place in the area.
The nickname of course is the WINDian Peaks!
We are at 10k feet. The Continental Divide is mere miles away as the crow flies. The wind is voracious. It was biting cold. She was not prepared at all in terms of knowing her gear, having it stowed the right way, etc. . Me, having that wonderful sense of patience and possessing an even temper that is the trait of my ethnic and/or family background (ha!), acted about as well as expected.
I could say how we both could have done things different (and we should have; we were both at fault in different ways), but it is easier to summarize it in one quick vignette.
The wind was howling so bad, I had to raise my voice to tell her how to buckle the snowshoes. She said "STOP YELLING!"
I said "I'M NOT YELLING!!!"
(bashful grin here)
We finally made it to the trees, where it was quite nice and protected from the wind.
Snow shoed to the hut (She did not ski) and had rather similar shenanigans going that I won't bore you all with. Low grade sniping, grumbling and grousing from both parties. Not our finest 48 hrs for either of us.
After the trip, we had a heart to heart and ended the relationship. For the first of many times over the course of two years. :)
Years later, I've learned more about functioning in the outdoors in terms of looking over gear for my trip partner and being diplomatic about suggestions as well. Out of that relationship I learned more patience and toning down some of the Northeast 'tude. Honestly don't think I'd be engaged today if it was not for that relationship 8 yrs ago.
So, not my best trip ever. But one of the most memorable. And, in many ways, one of the most important.