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Any ideas of how to develop this skill further without the sink or swim of trying to socialize out in the real world?
Not sure all my suggestions will fit thew bill, but here they are anyway:
1. Ask a work friend if they want to see a movie together after work some weekend.
2. Volunteer. Not all volunteer positions require a lot of interaction with people. Some require virtually none, some involve interacting with small groups of people (often the same people), and some involve a lot of interaction with a lot of people. Think about helping stock the shelves at your local food pantry, or volunteering to read stories to kids at the local library, or even something that fits a little more closely with what you do for a living. At the very least, it'll give you something to mention when people ask how you spent your off time as well as something nice to put on your resume. You'll know pretty quickly if you've found a good volunteer position for you, and you may be able to mold the position for your own comfort a bit since it is after all volunteer.
3. Think about joining Toastmasters. It'll enhance your public speaking skills, widen your network, and look good on your resume.
4. Take a class at your local community center or community college in something that has always interested you or even something job related. You'll meet people you share stuff with and possibly hear about opportunities you wouldn't have otherwise.
5. Join an interest group. Whether it's a book club that posted a flyer at your local library or a hiking club you found on Yahoo that does hikes in your area, it's an opportunity to meet new people and share an interest/new experience with someone.
If you have a friend you could convince to join you in any of these activities, that would be even better, as it would likely enhance your comfort level.