Written By: Robert Cocuzzo

The Boston Globe’s Love Letters advice columnist Meredith Goldstein answers love and relationship questions before appearing at the Dreamland on July 19th.

A decade ago, Meredith Goldstein pitched her editors at The Boston Globe about writing a local advice column that would focus on love and romantic relationships in the city. Love Letters debuted on the Globe’s website and quickly drew a devoted flock of readers who shared their own pieces of advice to the questions that came in to Goldstein. Today, Love Letters is one of the most widely read columns in the Globe and has recently given way to a wildly popular podcast. This spring, Goldstein reflected on her career as an advice columnist in her memoir, Can’t Help Myself. On July 19th, she will appear on Nantucket as part of the Dreamland Theater’s Page-to-Stage series to talk about her journey and to answer whatever questions your heart desires.

N MAGAZINE: You’ve spent time on Nantucket. What do you think are some of the pitfalls of dating on an island?

GOLDSTEIN: Once, when visiting Nantucket, I ran into the same person three times. Having an ex on an island — or a one-night stand on an island — must be an interesting challenge. I suppose you just have to know that no matter who you pursue, things might get awkward — unless you’ve already booked your ticket to the mainland. I imagine that dating as a weekend tourist on the island is a lot of fun.

N MAGAZINE: What’s one of the wildest questions you’ve received through your Love Letters column?

GOLDSTEIN: One of my favorite letters was from a woman who got physically intimate with a guy at his apartment and was upset that he didn’t call her an Uber so she could get home that night. She called her own Uber, but she felt that if he had been chivalrous, he would have called the car on her behalf. For me, it suggested that there were new codes of conduct for dating, based on technology. And I loved that so many commenters on the column said, “Hey, lady, call your own car.”

N MAGAZINE: What prepared you to answer people’s relationship questions?

GOLDSTEIN: I grew up with a single mom who was dating in the suburbs and an older sister who was very confident when it came to putting herself out there. Listening to them — and counseling them on their dating woes — taught me so much about what it means to advise and support without too much judgment. They trained me well.

N MAGAZINE: Is it true that most of your readers are married or in relationships? If so, what’s behind people’s fascination with single life?

GOLDSTEIN: Most Love Letters readers are in relationships (based on past surveys). I think they’re interested in the column because one, so many letters come from couples who are mid-relationship, and two, because in reading and talking about the problems, they learn more about each other. So many couples tell me that they read the letter together, and then come up with an answer as a team. It’s a fun game, to see whether their advice matches mine. In the end, they’re learning about their partners and practicing empathy, which I love.

N MAGAZINE: What are some of the best remedies you’ve come across in nursing a broken heart?

GOLDSTEIN: Music. I think music cures so much. And television. I always recommend a watch (or re-watch) of Buffy the Vampire Slayer. And taco salad. With guacamole.

N MAGAZINE: What are three of the most productive things you can do when dealing with a breakup and moving on?

GOLDSTEIN: One: Projects are good. It’s a great time to take a class, find a new workout routine, or start anything you’ve been putting off for a long time. Two: See friends. Call people and tell them you need company. There’s nothing wrong with connecting with people you may have ignored while in the relationship. Three: It is a loss, so give yourself time to grieve. Sadness is OK. Some people want to outrun the pain, but the only way beyond it is through it.

N MAGAZINE: What’s one mistake you think is most common in relationships?

GOLDSTEIN: People still expect their significant others to read their minds. Sometimes I want to say to a letter writer, “How about we just send this letter to your partner?” So much can be accomplished by a good, honest conversation.

N MAGAZINE: What are two ways of keeping a relationship exciting and fulfilling?

GOLDSTEIN: Spending free time alone is nice. If the only time you’ve spent with a partner is exhausted at home or running errands, it’s no good. At the very least, take a walk when you can. I also like the idea of sharing media, reading the same book or bonding over the same TV show. I love watching couples get animated when they tell me how they watch “Game of Thrones” or “The Crown” together. It’s a nice bonding thing.

N MAGAZINE: Are men and women really from different planets?

GOLDSTEIN: No. We’re all from Earth. It’s on us Earthlings to communicate well and to treat the people we love with respect.

N MAGAZINE: What’s your take on dating apps, and how do you think the search for love has changed in the digital age?

GOLDSTEIN: I love that online dating is no longer some embarrassing thing. Websites and apps make it so much easier to meet people, and that’s great. I do think those apps have made people lazier in person. I challenge all single people to look up from their phones and say hi.

N MAGAZINE: In your latest book Can’t Help Myself, you share your own personal relationships and experiences, including the loss of your mother. Was that process cathartic or unnerving?

GOLDSTEIN: Mostly cathartic. It was lovely to be able to admit to readers that I wasn’t always following my own advice. It was also time to tell them how the advice column helped my family. My mom and I would read their letters and comments in the hospital. We learned so much from everyone who contributed to Love Letters during those years, and I’ve always been grateful. Now they know.

N MAGAZINE: You’ve recently launched Love Letters into the airwaves in what’s becoming a wildly popular podcast. How has the medium changed the way you give advice, if at all?

GOLDSTEIN: I love being able to hear people’s voices, and to laugh and cry with them — in person. I also love the traditional letters, of course, but to sit next to someone as they tell me their relationship story? It’s an honor, and it’s so cool.

N MAGAZINE: Do you ever get tired of answering relationship questions?

GOLDSTEIN: No. And luckily people keep dating, falling in love and breaking up. It’s a pretty consistent business to be in.

Meredith Goldstein will appear at the Dreamland Theater on July 19th as part of the Page-to-Stage series. For more tickets and more information, click here.

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