I can role play combat wise, and guild wise, but the major problem for me is dialog, whenever I am talking to someone, or making a decision I always think: "What is the most logical thing to say" not: "what would my character say." I can never handle saying something I wouldn't, or make a bad decision because that's what my character would do, do you have anything to suggest to help me with this? Does anyone else find this difficult? How do you do it?

I understand what you mean. I sometimes struggle to be an evil bastard. What kind of character are you roleplaying?

What difference does it make? You rarely get more than one dialog option anyway and the results are the same even if you do.

If you're an evil and aggressive character: don't let them finish their line and kill them.

One of the best things to do in Roleplaying is give your character weaknesses, and choose options that would typically hurt or hinder them, even if you wouldn't personally do it.

Say you make a Khajiit that 'really' hates the color green. And you see a guy wearing the color Green, but he happens to be in your faction. You might personally not do anything, but for the sake of your character, you'd kill him, and roleplay getting in deep trouble with your guild.

That's where the fun in Roleplaying is, getting weaknesses. If you make a character that's perfect and godly, you'll never have fun.

Remember, the game is not real. All those people you kill and steal from aren't real. Always remember that, if you liked them, they will be alive if you play again.

I tend to imagine the convesation is a little bit more in depth than what is actually said in game. Then I base what I say on what my character feels, its pretty fun =)

I play Skyrim in order to immerse myself in makebelieve, not to exercise my fingers, so reminding myself that the game is not real diminishes my pleasure in it.

One way to get around dialogue that is difficult to make yourself say is to imagine that you're an undercover investigator, and only saying it to preserve your incognito. That Svana whatserface in Riften is going to get a shock when I am at liberty to express my true feelings, I can tell you.