Did you ever had that one time when playing D&D (IRL, Roll20, Discord, etc.) that pretty much leads to problems that just ruined it for you and your party?

From D&D side? Never. 

From player / DM side? Again and again. When other people start to get too incompatible at the gaming table because of their approach to the game or on an out-of-game level, it is rarely worth, keeping the group together. 

When my girlfriend said D&D was the work of the devil and get rid of all of my stuff.

Quote from Wysperra >>

When my girlfriend said D&D was the work of the devil and get rid of all of my stuff.

 So you got a new girlfriend I’m assuming?

One time my group was breaking into a prison to spring someone. It was very high security, and we were able to to bluff/disguise ourselves through the majority of the 15 levels, only getting in a few dust ups with some lower level guards when our cover story slipped, but otherwise making it through.

Except one player, a bard who tried to not take any damage spells and was looking for straight up battlefield control, but also didn't take any good control spells for this type of mission. For example, in one of the minor dust-ups she casts Fear on a prison guard that our barbarian could have two shotted, but now the guard is running and screaming down the corridor away from us in the direction of the guards we just slipped past, and he's forced by the spell to take the dash action every turn, so we have to take off and stop him from raising the alarm. My horizon walker didn't have his bow on him because he was posing as a prisoner being escorted, so I eventually had to blow a 2nd level spell slot on misty step to catch up, and then an ensnaring strike to stop him for the group to catch up. She keeps doing stuff like that throughout the mission, so by the time we get to the lower levels, I'm seriously lacking in spell slots from having to clean up her messes (she also is aware that she could've just dropped concentration on Fear to end the spell, she just chose not to because she didn't want to 'waste the spell slot'), and she's seriously lacking in spells cause she kept blowing 3rd and 4th level spells on the weak guards and takes forever to decide what to do when her turn (she has 1 damaging cantrip, dissonant whispers, but refuses to use it).

Despite all that, the group isn't doing badly health wise and the cleric still has a good amount of spells left, so we decide to just fight through the last two levels of the prison, that way we can all be prepared and have all our weapons on us and at the ready. So we engage the guards on the 13th level and me and the barbarian lead, each targeting a guard. I decide that now's a good time to cast hunter's mark, since at this point I can keep concentration up for an hour which should take me through to the boss. I take my turn, getting ready to kill the guard on my next turn when I get my Planar Warrior damage and hunter's mark damage combined, when the bard decides that this is the perfect time to use her last 4th level spell and slaps a hypnotic pattern on the whole room. Barbarian passes, the guard he's fighting fails, my guard passes...I fail. I automatically lose concentration on my hunters mark from going incapacitated, and the barbarian then attacks the stunned guard, un-stunning him (because they'd seen our faces so they kinda had to die, something the whole group was on board with so it's not like the bard was trying to spare their lives) so not only am I down to one remaining 1st level spell slot and one remaining 2nd level spell (which I want to save for emergencies and we *still* have a boss to fight), I'm now the only one actually still effected by the spell, which she still refuses to drop concentration on because she doesn't want to 'waste it', so I have to sit and wait while the barbarian solos both guards, the cleric spends his turns keeping the barbarian going, and the bard continues to do nothing useful. 

After that, I just didn't enjoy any of the remaining season. I really like my character in that game, but it's very rp heavy so I rarely get to really cut loose and stack my abilities in combat, so that series of really low stakes combats was a real treat, except we were constantly running damage control for the bard. And the whole time she kept being all "tee hee I'm so mischievous" like it was all in good fun, but I neither found it fun or funny. 

The next session when we fought the boss (a giant in guard armor,  accompanied by a mage and some ghosts) I had a little revenge in watching her complain about having no spells and not being able to do anything when I'd warned her that would happen before and she brushed it off saying she was a full caster and had spells for days, but mostly it was a week later and I had cooled off, and we still had a fun session. 

"Killboxes" for anyone who didn't do exactly what the DM imagined for his story. 8 inexplicably whittled down to 4 because of creative thinking - no saves if it wasn't part of his planned adventure. The final 4 wiped on an easy encounter, but I still suspect they just got tired of being railroaded and orchestrated their own demise to put the onus on the DM for it.

The DM never played with us again despite invitations. We assumed he was angry we ruined his story.

Was it not G. Gygax who stated something about D&D being cooperative? Can't remember the exact words.

Gygax actually thought that the game should be GM vs players and that a "lightning bolt from nowhere" could be used against PCs who didn't want to follow the GM's plot.

Anyway, moment that ruined a game for me: I was in a campaign where we had a bard who A) had for some reason prioritized boosting his strength and dexterity over his charisma and B) had not taken proficiency in any charisma-based skill besides Perform.

Despite this, in any non-combat encounter, the player would immediately try to take over and blurt out what his character was doing without ever giving any other players a chance to speak, despite the party also having a paladin and a sorcerer (the latter of which was my character) who both had higher charisma scores and proficiency in Persuasion and Bluff.  This meant that the party got into numerous fights that were completely unnecessary and we'd have been better off avoiding, because his idea of "diplomacy" was running up to NPCs and insisting that they tell him their stories so he could write songs about them, even if said NPC was a Stone Giant who was trying to meditate and flat-out told him that it wished for solitude.  But the real moment killer was when another player left the campaign due to having had a fight with a third player.  The departing player's character was immediately claimed by the bard's player, so now he had twice as much ability to hog the spotlight.  I tried to have a discussion with the player outside of the game (we've been friends for a long time) about the fairness of him running two characters and also about letting other players do things like speak to NPCs, but he took it the wrong way and started getting upset.  At that point I realized that I could either play D&D with him or I could maintain my friendship with him, but I wasn't going to be able to do both so I quit the game the next session.

"The essence of a roleplaying game is that it is a group, cooperative experience." -Gary Gygax

"Roleplaying isn't storytelling. If the dungeon master is directing it, it's not a game." -Gary Gygax

Seems the DM we had back then wasn't a subscriber to these thoughts. The DM is not there to tell a prescribed story nor force players to do something. Everyone is there to experience something together that was created cooperatively.