Margo Howard has warned us she may be a few minutes late for lunch at the Columbia on St. Armands because of a hairdresser’s appointment. “I always like to be prompt,” she emailed earlier, “but I’m reminded of one of my mother’s sayings: ‘He who is prompt is lonesome.’”

A memorable quote from any mom, but Howard’s mother was none other than advice columnist Ann Landers (born Esther Pauline Freedman and usually called Eppie), and Howard grew up hearing adages by the bushel. The only child of Eppie and her husband, Jules Lederer, Howard is a writer and former advice columnist who now winters with her husband, retired heart surgeon Ron Weintraub, on Longboat Key. She seems blissfully happy with him and their life, spent here and in Cambridge, Mass., but it wasn’t always so, as witness her 2014 book Eat, Drink & Remarry: Confessions of a Serial Wife, in which Howard talks about three previous marriages before hers to Weintraub stuck.

The book is anything but tragic in tone, however. Just a few minutes into our salads it’s clear that for Howard, a young-looking, flame-haired 76-year-old with delicate white skin (“I’ve never spent time in the sun,” she says—good advice there), a sense of humor about life and its mistakes is paramount.

If you grew up reading the Ann Landers columns, you’d expect that from Eppie’s daughter. Howard, whose previous two books, Eppie: The Story of Ann Landers and Ann Landers: A Life in Letters, were also memoirs, fell almost accidentally into the world of writing (snagging her first regular column for the Chicago Tribune while still in her 20s) and claims she is neither a researcher or a reporter. “What I find interesting is my own life,” she says. And when it comes to talking about that life, she is a raconteur par excellence.

Ask her about how her parents met, for example. “My father was a millinery salesman who sold her the veil for her upcoming wedding,” Howard says. “Obviously, he changed her mind.” The family moved a lot while she was growing up, with her father climbing the ladder from door-to-door salesman to founding Budget-Rent-A-Car International. They settled in Chicago in 1954, when Margo was 14, and while her mother was active there in society, volunteerism and politics, she grew restless and wanted more to do. (“My mother had amazing energy,” says Howard. “I’m low-energy—not like Jeb Bush, but not like my mother.”) When the opening to write the Ann Landers column arose, she competed in a blind contest and won.

For teenage Margo, the family’s lifestyle was frequently exciting. She refers to close Chicago friends like film critic Gene Siskel, columnist Irv Kupcinet and the Marshall Field family and to Hollywood stars including Lauren Bacall, Elizabeth Taylor (“She babysat me once in Palm Springs, when I was 12 and she was about 19”) and, of course, her third husband, the late actor Ken Howard. “Out of 14 years, we had 10 or 11 good ones,” she says.

While raising three children (with the help of nannies and nurses, she freely admits), Howard kept writing columns and commentary in publications from The Nation to People to The New Republic. She resisted doing an advice column, however, until her friend, Michael Kinsley (“the best editor in the country,” she says), convinced her to take over Slate’s “Dear Prudence” column, which she wrote for eight years before switching to a “Dear Margo” column on Women on the Web. She got out of the business in 2013 and says she’s no longer writing—“except for my tweets,” witty missives which she dispenses regularly on topics from politics to literature.

Otherwise, she reads, dines out, stays in touch with the many friends and acquaintances she’s made over the years—and now even gives advice to Sarasotans, below.

Dear Sarasota... We asked Margo some iconic local questions.

Q. I’m a trophy wife living in a beautiful Longboat Key penthouse—and I’m bored.

A. First, make it your business to find other younger wives. Then you’ll at least have a girl gang for lunch and shopping. If art interests you, there are Sarasota museums with which you could become familiar. Volunteering would give you the satisfaction of doing something for someone else. I hope that you have some interests, lest you give trophy wives a bad name. I suggest you pursue them—or find some. My mother always said there is no reason to be bored … and there isn’t.

Q. I’m an 81-year-old man living at Plymouth Harbor. My wife recently died and every woman here seems to be bringing me casseroles, dropping in to visit, and even making suggestive remarks. How do I deal with this?

A. Ah, the tuna casserole brigade has found a live one—no disrespect to your recently deceased wife. This is very common because women outnumber men. You need to stick up for yourself. If one of these women on the prowl becomes pushy, and you are not interested in spending time with her, simply say you’re still in mourning and, for the time being, prefer to go solo. I predict, in time, you will have a new lady friend that you chose—not one who chased after you.

Q. My husband fumes about the traffic whenever we go anywhere during season. How can I handle this, other than taking separate cars?

A. Might we be married to the same man? I’ve tried saying, “You know, no one can hear you but me.” I guess they just need to “vent.” The solution I have landed on is to not respond to the frustrated and complaining remarks, and just try to block them out. I read or play Solitaire on my phone. I suggest you do likewise.

Q. Yes, I have had a little “work” done, and it looks great. But what do I say if someone asks me about it and I don’t want to share?

A. Of course it’s rude to be asked, by all but your closest friends, but to deny the obvious is to, well, deny the obvious. To questioners who are not bosom buddies you might say, “Oh, just a little nip and a tuck.” Or “That is a rather personal question.” If they don’t back off, they are dim. To flat out deny it is to brand oneself a liar. Many movie people try the dodge of saying, “Oh, I’m wearing a new make-up,” or “I just took a vacation and had a good rest.” That is just ridiculous.

Q. As theater fans, we’re surprised that in Sarasota nearly every performance gets a standing ovation. We stand only when we feel a performance is exceptional, but we’re afraid we look rude staying in our seats. What should we do?

A. Stay seated. My husband and I, too, have noticed this odd new habit. A standing ovation for everyone and everything has rendered it meaningless. (And it’s not just in Sarasota; it’s a theater virus that has afflicted the whole country.)