Both personalization and utility value (UV) interventions have emerged in educational psychology as ways to increase students' interest in learning an academic subject, and potentially improve learning outcomes. However, empirical results for each approach have been mixed and these approaches have worked differently for different groups of students. In the present study, we combined the affordances of personalization with those of UV interventions to create novel activities where students posed mathematics problems based on their career and popular culture interests. While problem-posing has been identified as a powerful approach in the mathematics education literature, it is an effortful activity for learners, inducing demands described by theories related to desirable difficulties. We conducted a randomized control study with 458 middle school, high school, and college students enrolled in algebra courses with overlapping content to examine the impact of the personalized problem-posing intervention. Results showed that when controlling for dosage the intervention had statistically significant positive effects on algebra learning compared to a business-as-usual condition where students solved typical story problems in the same online platform. Posing problems based on popular culture interests was especially effective for learning for college students. However, for secondary school students, posing popular culture problems had significantly negative effects on their feelings of mathematics enjoyment. In addition, there was evidence that a subset of learners who completed a small dosage of the intervention had negative effects on their valuing of mathematics. Implications for interest development theory, personalized and UV interventions, and mathematical problem-posing designs are discussed.