I don't think drinking alcohol to get up the courage to go out is good advice. People tend to make bad decisions when under the influence of alcohol.
I think going out of your own town would be a good idea. Even if your presentation hides your identity when alone, your wife won't be in "disguise".
I also think going places where you won't have to interact with people is a better first time out than something like a restaurant where you have to talk to people and are stuck in one place for a half hour or more. Walking in the park, the city streets, a mall, etc. will be much easier and you can excape if you feel the need.
