This dissertation investigates gender differences in (1) retrospective (i.e., measured after task completion) item-specific confidence judgments, and whether these judgments were warranted. Of particular interest was whether gender interacts with problem difficulty to explain confidence, calibration (speaks to the accuracy of confidence judgments), and under/overconfidence. Furthermore, it examines whether, after controlling for confidence, there are gender differences in students' willingness to share math problem solutions, and whether this relationship depends on problem difficulty. This study analyzed confidence judgments and reports of willingness to share for 13 challenging math problems administered to 628 students enrolled in an undergraduate precalculus course. Results were that, compared to females, males tended to be more confident and more willing to share; however, as problem difficulty increased, the gender gap in confidence decreased. Females were found to be better calibrated than males, and this gap decreased with increasing problem difficulty. Additionally, the transition from easier to harder problems was accompanied by a transition from under- to over-confidence for females, but not males. Findings of this study have implications for how to support math learning for women and increase the retention of women in math-intensive STEM domains. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]