I stink at winging it- HELP!

[Dedekind]

The easiest solution for winging it for me is typically a roleplaying encounter. After that, a skill challenge would be good, particularly if the players are creative with their skills. I would avoid combat encounters unless the tangent the players want is definitely combat oriented.

(Coming up with an interesting and balanced encounter would take me at least 15 minutes. Sacrificing one of those things would save time, but then who wants to play an unbalanced interesting encounter or a balanced dull encounter?)

For NPCs, I also steal blatantly from books I have read that I know most of my players have not. There are some really good "characters" in both nonfiction and fiction, so give yourself wide latitude.

One of the things Patrick O'Brian does well is give characters modern day psychological or medical issues but, of course, nobody knows that these are "disorders" in the early 1800's. Examples:

1) Dyslexia (confuses left and right).
2) Type A or B personalities
3) Introvert v. Extrovert, and other Myers-Briggs categories
4) Asberger's (obsessed with seemingly mundane things, difficulty socializing)
5) Narcissim
6) Institutionalized

I even keep the character names, if they aren't out of place in fantasy.

 

[Longtooth Studios]

There is a ton of great advice here. The only thing I can think of to add is about being intimidated by players. Sometimes players can expect a lot. If you are locking up when you feel that you will get a lot of negative remarks from your players then that can be a big problem.
We want GMs to stick with the hobby and keep running games, and sometimes players lose site of this.
I have had players that made me feel really badly when I didn't run the game the way they wanted it ran. Those types of players need to be addressed and dealt with, possibly even removed from the table if you feel they will not see the trouble they are causing.

Not saying that is your issue, but it happens.

 

[knightofround]

Yeah, I wouldn't go as far as other people and state that you *need* instruction to improvise, or that you should run a fully improvised campaign. Becoming a good DM is just as much learning how to avoid situations where you have to wing it, as much as it is learning how to improvise.

Improvisation is a skill just like any other; some people are naturally good at it, and others aren't. Sure you could take classes, read a book if you want...but only do it if that's actually fun for you. God forbid your gaming becomes work! The same thing goes for over-preparing by pre-generating alternate storylines/encounters/characters ahead of time. That's work, not gaming.

Honestly, the thing that will help you the most is practice. Not only in DMing games, but also playing within them and watching how other DMs handle such situations. Nobody becomes a great DM right off the bat! Every single new DM I've seen, *every* single one sucked at winging it. Even some very impressive improv comedy friends of mine, because they didn't know how to wing a story or combat, they only knew how to wing characters and situations.

So you're not alone! Just stick out. Again, if it really bothers you, most metro areas have free improv classes, and there's plenty of good books and websites out there.

 

[Herobizkit]

One important technique to adapt is the ability to provide the "illusion" of choice. The players do not know 'what lies ahead' behind your DM screen. You could provide them with several options, though each eventually leads back to your main plot line... because they all lead back to your main plot line! It's kind of a dirty trick to do it all the time, but in a pinch, players like to choose options.

 

[ExploderWizard]

One important technique to adapt is the ability to provide the "illusion" of choice. The players do not know 'what lies ahead' behind your DM screen. You could provide them with several options, though each eventually leads back to your main plot line... because they all lead back to your main plot line! It's kind of a dirty trick to do it all the time, but in a pinch, players like to choose options.

Some players like their choices to matter. If they don't then don't bother offering them. I have a feeling that if the OP's players didn't want actual choices then he wouldn't need this advice.