Dear Prudence
A reader sought advice about their financial situation. They and their partner have saved $20 million, keeping their finances separate—a decision made by the reader. The reader, who has semi-retired and now does some consulting, enjoys life, while their partner remains in a high-stress job. Although both are frugal, the partner is particularly fixated on saving for retirement.
In their late 50s, the couple has no debts, and their house is fully paid off. The reader is concerned about how to convey to their partner that they have enough savings to enjoy life. The reader mentions coming from a background of poverty, while their partner had an upper-middle-class upbringing.
— When is enough?
— Dear Enough,
The $20 million figure is astonishing. You mention a partner, not a spouse, and it seems he might be holding you back from enjoying life. It may be worth reassessing the relationship if it’s dampening your joy.
A suggestion? Call some close friends and make a list of travel destinations you’d like to explore. Buy some new clothes and hit the road alone. You could leave your partner a list of household tasks and say you’ll reconnect later. Upon return, if he’s sitting at home eating leftover pizza and watching ads on TV because he refuses to pay for premium services, you’ll likely miss him a bit more after your adventures. Plus, his lifestyle may look less burdensome after your travels.
Dear Prudence
Another reader shared their upbringing filled with parental conflict disguised as normalcy. After their parents divorced, they recognized the importance of open communication. Now, living in a healthier environment, they face new challenges: they experience anxiety when tension arises at home.
While their parents check in on them regularly, the reader feels guilty about their feelings, torn between expressing their stress and wanting to appear mature. They wonder how to communicate their struggles without making it all about them.
— I can’t help but hear it.
— Dear I Can’t Help But Hear,
There’s no reason to feel ashamed about your feelings; your parents seem to want the best for you. When they reach out post-conflict, you might consider acknowledging your discomfort while recognizing their healthy dynamic.
If old fears creep in, think through those scenarios carefully. Reaching out to a therapist could provide valuable support. Try to express your thoughts in a way that doesn’t skew the focus solely onto you.
Dear Prudence
Another letter addressed a parent concerned about their daughter Annalize, engaged to two men. Initially surprised, the parent quickly warmed to both future partners. However, the reader’s husband is less accepting, expressing disgust and retracting financial support for the wedding he once promised.
— Trio Trouble
— Dear Trio Trouble,
If both you and your husband can access shared finances, go ahead and gift the promised amount to Annalize, Jacob, and Nathan. It’s your husband’s job to justify this change in plans. Consider suggesting that the engaged couple receive more since they have additional guests and involvement.
Classic Prudie
A reader revealed her husband wants to name their upcoming daughter after his ex-girlfriend, even though they have no contact anymore. It’s a complicated situation, and the feelings surrounding it are understandable.



