President Barack Obama signed two executive orders on Tuesday to mark “Equal Pay Day,” as the Democrats initiated a massive, coordinated, election-year move to win the vote of single women, a key demographic that could potentially allow them to win the Senate in November.

The first order forbids federal contractors from retaliating against staff who discuss salary information with each other, which one White House official said was “a critical tool to encourage pay transparency.” The other executive order extends equal pay claims’ statute of limitations.

“This is about Republicans seemingly opposing any efforts to even the playing field for working families,” said Obama, daring GOP resistance to the Paycheck Fairness Act, which would face a senate vote the next day. He argued their resistance would signify Republicans’ opposition to the economic interests of a vast amount of Americans. “I don’t know why you would resist the idea that women should be paid the same as men and then deny that that’s not always happening out there.”

Despite the huge push, the Democrats’ Paycheck Fairness Act failed to make it through the Senate on Wednesday by a measly six votes. If the bill had passed, it would’ve done the same thing as Obama’s first executive order, but for all employers in America–not just Federal employers. The bill would also have made employers liable to civil actions, and require the Equal Employment Opportunity Commission to collect pay information from employers.

The bill would have potentially helped close the wage gap women in America, which is now 77 cents for every dollar that men make. This issue, though, is not new by any means. The war for equal pay has been an uphill struggle ever since President Kennedy signed the Equal Pay Act of 1963.

“The Democrats’ strategy of pursuing an increase to the federal minimum wage, whether before or after midterm elections, may actually be a popular and sustainable idea for the national electorate.” explains Maria A. Sanders, COO and senior staff attorney for Legislative Intent Services, Inc. “State legislatures have been giving the idea serious and successful consideration. As of January 1, 2014, there were 21 states that had minimum wages above the federal minimum wage of $7.25 and there are currently 34 states considering increases to the state minimum wage.”

“Recent state enactments have passed tiered wage increase adjustments, such as California which will be increasing its minimum wage to $10.00, D.C. to $11.50, and West Virginia to $8.75, all by January 1, 2016,” continues Sanders. “So, riding on the coat-tails of these successful state measures to attract more voters may be a successful midterm elections strategy.”

It’s a risky strategy. Midterm voters are typically older and more male, but the Dems believe that the key demographic for electoral victory is single women. After all, exit polls from Obama’s 2008 election showed that it was won with the support of 58% single women, and in 2012, Obama won 67% of single women. Despite these facts, the strategy is still unproven.