Question: I’m dating a much younger woman. How do I navigate the age gap?
Brian, West Chester, PA
Assuming she’s not jailbait, your best move in this case is no move at all: Just relax and keep having fun. I know some older women who act like Alpha Gamma Delta pledges, and a whole bunch of 20-somethings who could outclass Duchess Kate. No matter how wide the age gap, you two need more weekends together to figure out whether your maturity levels and life goals align. Age won’t tell you that. Time will.
Question: I’m worried she won’t like the family ring I’m proposing with. How do I find out without ruining the surprise?
Terrence, Evanston, IL
Here’s a better question: How do you like the ring? An heirloom has meaning, and that should be more important to her than the ring’s style and number of carats. But if you’re that nervous, recruit one of her close friends, who will be happy to feel her out without spoiling your big moment.
Question: I’ve fallen for my best friend, but she has a boyfriend. Should I speak up?
Rick, Spokane, WA
Life isn’t a Nicholas Sparks novel. In the real world, trying to date your best bud usually ruins a friendship—especially if she’s seeing someone. Willing to take that risk? Then be blunt. Explain how your feelings have changed and tell her exactly what you want. Plus (this is important), give her the option of letting you down easy and staying friends—but only if you mean it.
