The Most Important Thing About Dating

Meredith Goldstein is an advice columnist and entertainment reporter for The Boston Globe. Her love advice column “Love Letters” appears daily on Boston.com and in the Globe’s print edition every Tuesday, Friday, and Saturday.

Meredith’s first novel The Singles was released by Penguin/Plume in 2012. It’s about the only five dateless guests at a wedding. Her next book is a memoir, based on “Love Letters,” which Grand Central Publishing will release in 2018.

In a recent interview with SpeakEasy, Meredith answered some Significant Questions about dating and weddings raised by the play Significant Other.

SPEAKEASY: You have been offering relationship advice for some time now. What would you say is the question you get asked the most often, and what has been your response?

MEREDITH GOLDSTEIN: I’ve written the column for seven years, and every year I’m shocked by how many people write in because their partners haven’t said “I love you.” I could have a spinoff column about hearing those three words. My answer for those people is that “I love you” doesn’t answer every question. If you’re desperate to hear those three words, there’s something else missing in the relationship.

SE: What would you say is the one most common mistake people make when dating?

MG: People assume it’s supposed to be easy. Sometimes it is, but usually it’s not. You have to be prepared for work.

SE: In your opinion, given all the cultural and technological changes in American society, is it easier or harder today to meet that special someone?

MG: It’s easier these days. Sometimes I despise what technology has done to human interaction, but I can’t deny that it’s made it easier for busy people to find one another.

SE: How has technology changed the way people meet and date today?

MG: It’s forced us to be better writers. If you’re a bad texter, it’s hard to date. If you can’t draft a good profile for yourself, it’s hard to meet the right people. You have to be able to write your way to an in-person meet-up.

SE: What are some signs that the person you have been dating could be THE ONE?

MG: I don’t believe in “the one.” That said, if you see your partner do or say something gross and you’re able to forgive (or find it endearing), you’re on your way.

SE: Jordan Berman, the main character in Significant Other, is 29 years old when he decides to jump back into the dating pool. What advice do you have for someone that age who is feeling a little panicked about their chances for ever finding love?

MG: I write this as someone who just turned 39: I hate ‘9s. Nines will drive you crazy because they force you to notice what’s missing. It’s hard to believe, but 30 feels better than 29. That’s what I tell my readers.

SE: At one point Jordan develops a crush on a hunky co-worker. Is it ever a good idea to date someone you work with?

MG: Many of my readers would disagree, but I say go for it. I know too many fantastic couples who met at work. If you’re really into a coworker (and the feeling is mutual), it’s worth trying. Just follow the rules—and be a grownup if it doesn’t work out.

SE: If you are interested in someone, but are not sure if they share the same sexual orientation, how should you approach?

MG: It all depends on how well you know the person. I’ve asked people if they have a partner, and usually they give an answer that clarifies.

SE: What is your advice for someone feeling lonely because his or her BFFs are all suddenly seriously dating or married off?  

MG: Find more single friends. Expand your circle. I’m not saying you should ditch the marrieds, but it’s important to seek out some new friends who share your experience.

SE: Is it ever okay to skip a good friend’s wedding?

MG: I’ve done it, but I don’t recommend it. From my experience, no matter how awful you feel about being single at a wedding, you’ll never regret going, but you might regret missing out. Also, you never know who you’ll meet at a wedding.

SE: What was the worst wedding you ever attended and what made it so memorably bad?  

MG: I don’t think I’ve ever been to a terrible wedding, but I have been terrible at wonderful weddings. I was terrible at one of my best friend’s wedding, which is why I wrote The Singles. The book is fiction, but … also not.

SE: Jordan’s grandmother tells him that “the most important thing” is to find someone. Do you agree?

MG: The most important thing is to find people. Find your people and you’ll be OK.

SE: Are there really “plenty of fish in the sea?” as our mothers would have us believe?  Do you believe there is someone for everyone?

MG: My friend Danielle taught me the expression, “The odds are good but the goods are odd.” That says it all.