How do I ask my date to split the dinner tab?

QI’m a 50-year-old guy who’s been divorced for about a year. I’m beginning to date again, but I’m uncertain who pays for what. A friend tells me that he always pays for the first date when he goes out to dinner with someone new. But after that, he splits the check 50/50, unless there’s a special reason not to, like it’s her birthday. This sounds reasonable to me. But what should I do if, on the second date, the woman doesn’t reach for her wallet as I reach for mine? My friend said he just tells his date, “It looks like your share’s about $X” and hands her the bill. I’m not sure I’m that brave.

AWe once heard a female comic say, “Of course, I’m a feminist. Not a buy-my-own-drinks feminist, but still a feminist.” Our point is, you’re right to be concerned that some of the women you date may be slow to reach for their wallets. But fear not. You’ll find your own voice for proposing to split the dinner tab as the dates — and the bills — start to pile up. Just to be clear that there is nothing wrong with asking a woman to pay for her share of dinner. The problem with your friend’s “50/50 after the first date” rule is that one size does not fit all. Au contraire.

Even by the second meal out, you’ll probably have a more nuanced financial relationship with a new or prospective romantic partner than you do with, say, a friend at work. So instead of worrying too much about when and how to ask your date to get out her credit card, spend more time considering how you’ll want to handle the situation if you begin seeing someone regularly who has significantly less — or significantly more — money than you do. Happy hunting, Romeo.

QYou recently published a letter from a woman whose sister claimed the letter writer had “stolen her life.” (When the letter writer was 10, their parents had suffered a serious financial reversal and her still-resentful, much younger sister missed out on the advantages she had enjoyed, such as living in a big house and going to private schools).

I hope I don’t sound paranoid, but I’ve seen how these “stolen life” remarks can turn from words into deeds. For example, the envious sister might decide that, if their now-elderly parents need financial assistance, only the older sister is obligated to help, the sisters’ respective financial resources notwithstanding. Or the envious sister might insist that she’s entitled to more of the parents’ estate, even though their wills say otherwise. I know it sounds crazy, but I have seen this time and again. My point is, I think the older sister needs to steel herself for worse to come. Do you agree?

AWe do. Old grievances have a way of bubbling to the surface — and becoming weaponized — at moments of family crisis or transition. You and the Boy Scouts are right: “Be prepared.”

Jeanne Fleming and Leonard Schwarz are Palo Alto-based columnists and authors. Please e-mail your questions about money and relationships to Questions@ MoneyManners.net.