My Love for You is Like a Truck is Barbarian (the DW Barbarian is probably the best incarnation of a D&D offering that would live up to the tropes of Conan in play).
Old Enemies and A Lover in Every Port is Dashing Hero playbook. Classic Zoro, Dread Pirate Roberts/Man In Black/Errol Flynn tropes. Its easily my favorite Dungeon World playbook. I did a two-off Sword and Sorcery/Swashbuckling mash-up with it and the Barbarian and it was glorious.
So question for everyone (especially [MENTION=29398]Lanefan[/MENTION] , [MENTION=6785785]hawkeyefan[/MENTION] , [MENTION=6802765]Xetheral[/MENTION] , [MENTION=6778044]Ilbranteloth[/MENTION] ). When you're running your D&D games (5e or whatever), do you guys "ask questions and use the answers." For instance:
GM: "An anxious looking fellow enters the tavern while looking this way and that. He runs headlong into a barmaid's tray due to his state. They both hit the deck and drinks spill everywhere. While he's sitting his head is still scanning left and right as he absent-mindedly mats the liquid into his soiled shirt. He locks eyes with you and breaks into a crawl which leads him unsteadily to his feet. He's making a bee-line for your table."
"Who is this guy? Do you know him?"
Not often. At least not the "Who is this guy?" approach. I tie things into backgrounds, or into things that the players may have said (and often don't remember), things like that all the time. My goal is to have them grounded in the campaign as much as possible, particularly the mundane aspects of life.
A lot of that has to do with the players themselves, most of them are looking for me to provide answers to questions like that. If a group is more receptive to having a greater amount of world-building from the player side, I'm open to experimenting. But it doesn't happen frequently.
I'm always asking them to feed me more information about their background and character's likes, dislikes, etc. I give them quite a bit of leeway on their background, along with input and guidance. This includes a willingness to consider out-of-class abilities, magic items, better equipment, etc., even at 1st level.
For example, my daughter loves dinosaurs and wanted a pet deinonychus. She also wanted a character similar to Arilyn Moonblade, among other non-D&D sources. So she's an elven druid of Selune, but started off in Evereska with her parents. Due to the attack by the phaerimm and some other (later found out to be distant family) concerns, her mother pushed her through a portal with her moonblade (with seven runes). She found herself alone in the jungles of Chult, unable to even touch the bare moonblade without taking damage. She met a druid who cared for her and trained her, until they were able to find a portal (about 10 years later) that returned her to the North (in Icewind Dale) where the campaign was starting. So she doesn't have a pet deinonychus, but she can change into one.
This was all for the start of the campaign, largely written by her, with my input into how it could tie together. So among the things she was immediately concerned with was to find out if her mother (and family) was alive, and to learn about this sword, and hopefully learn to wield it. Until then she couldn't even use it in battle. Things expanded as the campaign progressed, and then the character switched over to another campaign (same Forgotten Realms and time, just different players). She was also constantly concerned about keeping the sword, and herself, secret because she was concerned that there were others looking for her or the sword (and as time went on there was some evidence of that). She has a great imagination, so a lot of the twists came from her, even if she didn't always remember that she said them.
So I'm quite willing to give a lot of leeway, and go well beyond what would be considered overpowered for 1st level, or even higher level characters. The moonblade has a history of being used in her family to battle fiends and undead, and many of the abilities were related to that aspect. But until she was able to actually attune (and be accepted) by the sword, she used it in other creative ways. My (and her) favorite was when she "accidentally" dropped from carrying it on her back, so that a sorceress they were fighting would pick it up, taking damage in the process, and giving an opening for the others in her party to take advantage of.
Something closer to your question was when a new antagonist entered the campaign, the brother of the character's ex-wife (he had specifically added "divorced" to his character during creation). So he helped provide much of the backstory of the ex-brother, which I expanded upon. I will note that most of the time I expand on their stories quite extensively, way beyond what they probably think would be approved for the campaign. So I guess it occurred something along the lines of, "you recognize the man, as you know him quite well as your ex-brother in-law. Why is there bad blood between the two of you?"
The reason I wanted him to take the lead there, is that it gives me a more personal thing to work with - if I knew why he (the player) would think that there is bad blood there let me exploit it better in the future. I then tweak it from there.