earn about 65K per year. became a widower this year so will file single. have about 20K in medical expenses. Also have a lot I plan on donating to...

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Hi Brian, 

f your spouse died during the year, you are considered married for the whole year for filing status purposes.

  If you didn't remarry before the end of the tax year, you can file a joint return for yourself and your deceased spouse. For the next 2 years, you may be entitled to the special benefits described later under Qualifying Widow(er) With Dependent Child .

With that said you should use this link below including her income to determine what your tax return will look like. 

https://turbotax.intuit.com/tax-tools/calculators/taxcaster/

Hi Brian if your only goal is to maximize potential tax deductions then those deductions would likely be better during the 2017 tax year since your AGI and standard deduction will likely be lower