I read your RP guides recently and thought of a question. Do you have any advice for people who have trouble separating their characters from themselves and end up practically with a self insert? (Love Milo's story, btw. :))

Two suggestions.

The first is, go for it. In a D&D game, it’s easiest to accurately RP if your character is similar to yourself. I find it really hard playing evil characters even in video games for that reason—I just like rescuing people in games. Create good reasons for why your character would have traits similar to those you find easiest to play (similarly, I tend to play characters who are rash, take risks, and are impulsive, just because that’s how I tend to strategize, as well).

My other idea to help keep your character separate from yourself is to make them different in ways that are largely set in stone that you have to deal with. The most effective way I’ve found is to play a character of a different gender, or one who is really, really prejudiced against elves (or dwarves, or whatever). By making your character’s starting position very different from your own, it will compensate, in part, for your natural tendency to make your character more like yourself.

Still, this is a problem I grapple with as well. Optimizing the numbers, and leading the party into comedic and/or epic situations, comes to me much more naturally than roleplaying.