We’re kicking off this week with some listener feedback on good problem to have – adjusting to earning enough money for more than just the essentials of life! And then, professional trans lesbian Elizabeth Mills joins to respond to your letters! First up: My sister is asking for cash for Christmas, but I’m afraid I’d be enabling destructive habits. What’s the right gift? My fiance doesn’t want me to stay friends with someone I hooked up with once. Help! My ailing sister moved home after a life of ignoring me and expects me to see to her every need! Help! And finally: How can I let go of my worries about being “too feminine” to be trans? Hear more Prudence by joining Slate Plus: Slate.com/Prudiepod.