I’ve always been a “fixer.” When my boyfriend, Leo, spent months venting about his family’s financial struggles—how his parents were skipping meals and his younger sister, Sylvie, had never seen the ocean—I decided to do something big. My mom works as a high-level manager for a luxury all-inclusive resort chain, and she managed to get me a “friends and family” rate that turned a $10,000 vacation into something I could actually afford.