Not sure what to do... kind of a unique situation. I was an employee with a real estate agency from 8/10 - mid Dec. 2010. Made ZERO income (just started - training). Mid-December 2010 we all got "technically Let Go" and we became Independent Contractors.

Do I fill out a Schedule C for "self employed" because I legally was before the end of 2010... OR do I have to fill out a Form 2106 for Unreimbursed Business Expenses?

Question 2 - Boyfriend worked for same real estate company, BUT he received a W2 with income. He also became an independent contractor mid-Dec 2010 BUT had no income so didn't receive a 1099-MISC as well. Which form does he use for business expenses?

Actually, it is pretty simple:

- YOUR expenses are documented on the Schedule C. Since you had no income from the Schedule C position, you will show loss against other income.

- The boyfriend has to show the expenses using Form 2106 for the expenses incurred prior to 15 December 2010. He can use the Schedule C for the post-15 dec 2011 expenses as well.