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Handing her money in public embarrasses her. This older man needs to be tactful when he hands her money in private. A gift of money should be in private.

January 22, 2017

One day, when I owned Tutor and Spunky’s, my Dana Point deli, I noticed a man and a woman seated in the dining room but thought little of it, other than I noticed that the man was eating an entire quart of chili on his own.


Ten minutes later, the woman poked her head into my office. She said, "I'm Angie. I know you write that dating column and wanted to ask you a question." The man she'd been with had already left the deli and was waiting for her in his large white pickup truck in the parking lot.


Angie said, "That man I was having lunch with is 22-years-older than I (she looked to be about 50). Out of kindness, he likes to give me money, which I appreciate. He expects nothing in return. He knows times are a little tough for me these days.

Who pays for the date?

September 22, 2009

A controversy started during a speech I was giving at the Laguna Niguel, California, Library to a group of 90 middle-aged and senior singles, on the topic: how baby boomers can meet a mate.

When I said, “Women should be willing to ask a man out and pay for the date,” a woman in the audience whispered to the woman seated next to her, “It’ll be a cold day in hell before I pay for a man’s dinner.”

Single senior shares the male point of view on senior dating. Reflections on who pays for the senior date?

December 01, 2016

Comment from Tom: There are two parts to this column. Part One is Rich’s Male Point of View.

Part Two is the responses from newsletter readers the following week. Fun to read the before and after.

Part One – Rich’s Male Point of View
One of the complaints I hear from single women is that we don't hear much from single men. Today, we address that issue.
I have a friend we will call Rich. At the end of this article, he explains why he didn't want his real name used. I will say he lives in Orange County in Southern California. Rich emailed in a response to a number of recent newsletters. He didn't have any axe to grind, nor did he focus on any one topic. He just shared some of his rambling thoughts on being single from the male point of view.


Does Your Senior Partner Share Expenses

August 04, 2016

Katie is a bright, intelligent and attractive woman. She's a published writer; I've seen her articles. Katie responded to my recent column about couples sharing expenses.

"I've been paying more than half of EVERYTHING (and always have) with my current dating partner of several months and he still complains -- vacations, meals, etc. He NEVER offers to pay for daughter-in-law, not even on a special occasion, not even a birthday gift. He and I live about an hour apart and I do more than half of the driving. I know, I know, the problem is me and my choice."

I said to Katie, "I can't imagine a fine woman such as yourself doing more than your share of driving to a man's house or having to pay more than half of the expenses."

Dating info and advice for widows, widowers, divorced men and women and people never married

July 31, 2016

Note from Tom: This article appeared in September, 2003, in response to the article about sharing dating expenses from the week before

Readers sound off about sharing dating expenses. Man who broke up over sharing expenses finds both support and criticism

In last week's column, Ben, 50, of Dana Point broke up with his 46-year-old girlfriend because she wouldn't share expenses and wouldn't share in the driving between their homes. Readers responded in droves, the majority of them women.

Senior dating issue: Sharing dating expenses

July 31, 2016

A year ago, Ben, 50, of Dana Point asked for my opinion about his 46-year-old girlfriend sharing dating expenses.

I told him that was for them to work out.

He recently e-mailed, "I finally brought up sharing expenses and she agreed. Well, we went on a cruise and I paid for all of the expenses. She still hasn't paid her part, about $520. I also pay most of the time when her two sons go out with us. A friend suggested I give her an invoice.

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