Two studies explored gender-relevant expectations and consequences of seeking flexible work arrangements. Study 1 examined preferences and expectations of students nearing the job market. While men and women valued work flexibility and work–life balance equally, women reported greater intentions to seek flexibility in their careers. Intentions were predicted by projected perceptions on gender-relevant traits. In Study 2, participants evaluated hypothetical targets who sought a flexible work arrangement after the birth of a child. Flexibility seekers were given lower job evaluations than targets with traditional work arrangements; however, they were also seen as warmer and more moral. Men may be particularly penalized at the character level, as flexibility seekers were seen as less masculine and rated lower on masculine prescriptive traits and higher on feminine prescriptive traits. Together these studies suggest that while men value work flexibility they may be reluctant to seek it because of (potentially well-founded) fears of stigmatization.