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Dating While Gray™

Dating While Gray™

Laura Stassi

Relationships, Society & Culture

4.4650 Ratings

Overview

When writer Laura Stassi’s marriage ended after nearly 30 years, she asked friends and relationship experts for advice on navigating the dating scene. On Dating While Gray, Laura shares what she’s learned: love doesn’t get easier as you get older.

127 Episodes

Another Dating Point of View

Laura chats with Julie Krafchick and Yue Xu, co-hosts of the Dateable podcast and authors of “How To Be Dateable: The Essential Guide to Finding Your Person and Falling in Love”; and It’s Just Lunch and 33,000 Dates founder Andrea McGinty, author of “2nd Acts: Winning Strategies for Dating Over 50.”

Transcribed - Published: 27 February 2025

A Little Love Help from My AI Friend

Is artificial intelligence in your dating toolkit? After avoiding the topic, Laura explores. She talks with Igor Khalatian, tech entrepreneur and founder of Iris Dating, and gray dater Emmay, who’s using ChatGPT to help her craft flirtatious messages with potential matches.

Transcribed - Published: 20 February 2025

Together and Apart: Two Updates

On the eve of Valentine’s Day, Dating While Gray continues its year-round mission of offering insights and advice on love, sex, and relationships for people of a certain age. On this episode, Laura checks in with two gray daters who previously shared their compelling true stories. Has Betty’s whirlwind, pandemic-born romance stood the test of time? Evelyn and her partner are enjoying living side by side in a duplex But did the courts give it the official Live Apart Together kiss of approval?

Transcribed - Published: 13 February 2025

Love Across the Divide, Part 2

Laura talks with psychotherapist Ken Page about older romance and bridging political differences in kinder and gentler ways. Plus, listeners weigh in on labels like feminist and woke. Bonus content: We hear from Jeanne Safer, author of “I Love You, But I Hate Your Politics.”

Transcribed - Published: 21 November 2024

Love Across the Divide, Part 1

If romantic relationships are built on shared values, does that mean two people need to be aligned politically to have a deep connection and strong bond? In Part 1 of the Dating While Gray/APM broadcast special, Laura talks with older Americans navigating red-blue romance … some more successfully than others.

Transcribed - Published: 14 November 2024

The Intentional Love Journey

Looking for a soul salve? Here it is: Four stories of romance seeking and finding, shared by show listeners. They include Anthony, who won’t let heartbreak interfere with progress; and Peter, who describes his “good enough” union in the most positive of ways.

Transcribed - Published: 7 November 2024

Laura’s Podcast Pick: To See Each Other

Laura shares “A Beloved Nursing Home,” which kicks off Season 2 of tTo See Each Other. Show host George Goehl travels to Lincoln County, Wisconsin, to get to know a colorful group of people who are fighting for the future of the last remaining public nursing home in the community.

Transcribed - Published: 31 October 2024

Romantic Love in Limbo

It’s the dating situation no one dares think about … until it happens to them. Laura discusses ambiguous loss and next steps with Mike, whose wife has been diagnosed with a terminal brain disease, and marriage and family therapist Linda Hershman.

Transcribed - Published: 24 October 2024

The Stay-or-Go Dilemma

Is there ever a right time to end a romantic relationship – especially when there’s a lot of history involved? Chris and other listeners share their struggles, plus Laura chats with marriage and family therapist Linda Hershman about discernment counseling.

Transcribed - Published: 17 October 2024

Ready, Aim, Swipe!

Dating sites and apps can be a huge time suck and overwhelmingly, users report feeling burned out. Should we trust our gut and make quick swiping decisions? Or does being more thoughtful about the process lead to love success? Laura talks strategies and outcomes with relationship coaches and online soldiers.

Transcribed - Published: 10 October 2024

Listener Mailbag

Laura shares comments and questions from listeners responding to previous DWG episodes.

Transcribed - Published: 3 October 2024

Love, In So Many Words

Laura chats with novelist Susan Coll about the inspiration behind her novels featuring protagonists in dysfunctional relationships. Plus, a poet captures the ups and downs of her love life, and a retired biotechnology writer turns to penning “elder erotica.”

Transcribed - Published: 26 September 2024

Advice from a Sex Journalist

Using toys, getting STI tested, embracing the use-it-or-lose it mantra … Laura shares excerpts of a candid Facebook Live event with Michael Castleman, a longtime sex journalist and author, most recently, of “Sizzling Sex for Life: Everything You Need to Know to Maximize Erotic Pleasure at Any Age.”

Transcribed - Published: 19 September 2024

Inside the Lives of Older Singles

The Golden Bachelorette premiere is approaching! Laura wonders if this time, the reality show will be more, you know, real. She also shares excerpts from “Beyond ‘Reality’ TV: Inside the Lives of Older Singles,” a Dating While Gray/American Public Media radio broadcast special.

Transcribed - Published: 12 September 2024

Life After A Gray Divorce

In Anita's lifetime, the divorce rate for Americans over 55 has doubled. People are living longer, divorce stigma has decreased and women are more financially independent. But leaving a decades-long marriage … is a big life upheaval. Anita gets personal accounts from two gray divorcees about what it was like to rebuild their identities, finances and freedom post-divorce. They discuss money management, surfing and why women initiate divorce most often in heterosexual partnerships. Meet the guests: - Laura Stassi is a writer, editor and the host of the podcast "Dating While Gray." - Dr. Stephanie Han is a literature scholar, award-winning author and educator. Special thanks to Nanette Murphy and Linda Lingo for sharing their thoughts for this episode!

Transcribed - Published: 5 September 2024

(Encore) Starting All Over Again

Pilot episode! Laura attends her 40th high school reunion, where her former classmates open up about their own love lives and dating strategies. Then, she revisits a man she went on a date with to get schooled on online dating and the “three-date” rule. Finally, Laura gleans inspiration from a couple who met at the apartment building where they both liv

Transcribed - Published: 29 August 2024

(Encore) Pants on Fire

Can we keep the love faith while circumventing the deceivers? Security analyst Kim Key offers advice and tips on avoiding online romance scams, based on her research and reporting for PCMag. Then, Laura hears about conducting background checks on potential dating partners from listeners including Paula, who says it’s her new M.O. after her experience with a suspiciously eager love interest. Finally, journalist and “Duped” author Abby Ellen shares about uncloaking her former fiancé. She wonders if he’s simply larger than life; turns out he’s a lying liar.

Transcribed - Published: 22 August 2024

(Encore) Sage Advice

Words of romance wisdom from: Writer Sophy Burnham, who offers insights based on decades of personal experience; Leora Hoffman, an attorney-turned- matchmaker who built her business while finding a partner for herself; DWG listeners; and marriage and family therapist Katherine Woodward Thomas, author of “Calling In The One" and "Conscious Uncoupling." 

Transcribed - Published: 15 August 2024

(Encore) Romance and Money

Laura talks with Shawn Leamon, a financial expert who usually explores money from an uncoupling point of view. Shawn offers tips and advice to Laura's other guests: Ginny, who's been so financially burned that she literally can't afford to be vulnerable; Sue, who's finding trouble meeting someone whom she considers her financial equal; and Barry, who blames his debt-free but modest lifestyle for his lackluster love life.

Transcribed - Published: 8 August 2024

(Encore) Love in the Stars

Laura’s a Scorpio, and she reads her horoscope every morning for fun. But is there more to astrology than sun signs, and can it help us make romantic connections? Laura talks with Koku, who looks to the zodiac as a “quiet consultant” in her life. Then astrologer Leslie McGuirk says sun signs and daily horoscopes can be entertaining, but there’s a lot more to it than that. After, Laura meets with a self-taught chart reader to learn what might be in the stars for her romantic future. Mr. G, Mr. T or Mr. W – whose planets are best aligned with Laura’s?

Transcribed - Published: 1 August 2024

Speed Dating While Gray: The Happily Ever After Journey

Jerry’s in his early seventies when friends introduce him to 65-year-old, never-married Ann. They share with Laura the twists and turns of their romantic relationship.

Transcribed - Published: 25 July 2024

(Encore) Dating 101: The First Date

Coach Amy Schoen returns for do’s, don’ts, and dishing with host Laura Stassi and Paulina, who can’t figure out if dating is different because she’s older, or because she’s dating Americans. What is a date, anyway? Then there’s Glyn, who offers cautionary tales about manners, and menu choices. Finally, we hear from Paula, who recounts that time she fielded a highly personal question.

Transcribed - Published: 18 July 2024

Speed Dating While Gray: When A Helper Needs Help

Laura chats with Kerry, a psychotherapist whose hopes for romantic companionship are faltering.

Transcribed - Published: 11 July 2024

(Encore) Boomerang Love

Who hasn’t done a little digging to find a flame from our younger years? But, as Laura discovers, taking the next steps to reach out is when things can get complicated.

Transcribed - Published: 4 July 2024

(Encore) Unexpected Love

Are you starting to fret that despite all of your efforts, you’ll never find The One? Here’s a little inspiration to relax and just let it be: three stories of not seeking love, but magically finding it.

Transcribed - Published: 27 June 2024

Speed Dating While Gray: The Only Ring is from a Phone

Shared mission, different game plan: Laura chats with Caitlin Pierce, creator of the reality dating show Hang Up from Radiotopia/PRX.

Transcribed - Published: 20 June 2024

(Encore) Clicking, Swiping, Boosting, Super Liking

Since the first modern dating website was created in the mid-’90s, millions of people have spent a lot of time, energy and dollars. So why is the jury still out on whether technology actually leads to lasting love connections?

Transcribed - Published: 13 June 2024

Speed Dating While Gray: Finding Home

Laura gets insights from Ryan Frederick, author of “Right Place, Right Time: The Ultimate Guide for Choosing a Home for the Second Half of Life.”

Transcribed - Published: 6 June 2024

(Encore) Making Moves

Laura talks with Carson, whose change in relationship status sparks a cross-country move. Then, Laura hears from unlucky-in-love Albert, who wonders if it makes sense to re-establish himself somewhere other than his longtime hometown to find what he’s looking for, relationship-wise. For advice, Laura taps Bill Chopik, associate psychology professor and director of Michigan State University's Close Relationships Lab. Finally, Laura meets up with Margo, who lives in the big rig she drives cross-country for her career. Margo loves her life behind the wheel but is starting to think that for her personal life as well as dog Xander’s well-being, it might be time to come off the road.

Transcribed - Published: 30 May 2024

Speed Dating While Gray: Not All Who Wander …

Laura chats with Stephanie, who’s living around the globe on a budget after divorce and retirement.

Transcribed - Published: 23 May 2024

(Encore) The Older Brain on Love

Remember the PSA that aired on TV for years, with the egg and the frying pan: This is your brain, this is drugs, this is your brain on drugs? It seems like love can be a lot like that, too, even when we’re older. Why? For answers, we turn to perhaps the premier expert on the brain and love: Helen Fisher.

Transcribed - Published: 16 May 2024

Speed Dating While Gray: Tell Meredith Goldstein All About It

Laura chats with one of Dating While Gray’s role models: Meredith Goldstein, Boston Globe advice columnist and host of the Love Letters podcast.

Transcribed - Published: 9 May 2024

Laura’s Podcast Pick: An Arm and a Leg, The Medicare Episode

Medicare is more complicated, and expensive, than many people realize. Also, it’s not too early to start thinking about this benefit. An Arm and a Leg host Dan Weissmann gets the scoop from Sarah Jane Tribble, who’s been covering the story for KFF Health News and the Washington Post.

Transcribed - Published: 2 May 2024

One Love, Two Homes

A growing number of older couples are not sharing space 24/7. It’s called living apart together, or LAT. Anthropologist Helen Fisher reveals her LAT arrangement with husband John. Then Laura chats with Vicki Larson, author of the forthcoming “LATitude: How to Make a Live Apart Together Relationship Work.” Finally, an LAT arrangement involving a duplex sparks a courtroom battle.

Transcribed - Published: 25 April 2024

Smoke … and Mirrors

Ahead of the international get-high holiday of 4/20, Laura chats with cannabis researcher Dr. Peter Grinspoon. He also has thoughts about dating. Plus, the Golden Bachelor couple announced they’re getting divorced. Did you see it coming? Listeners – and Laura – have thoughts.

Transcribed - Published: 18 April 2024

Anatomy of a Fall

Crystal and Dave clicked! First online, and then in real life. Are they moving too fast? Have the red flags been flying all along? Laura talks with each of them about their relationship journey.

Transcribed - Published: 11 April 2024

Love Is A Family Affair

Sydney helps mom Jennifer navigate the dating apps. Widower Herb offers daughter Jen tips for a successful long-term relationship, even as bad timing keeps him apart from his longtime love. Both stories prove that the ties that bind us need not be restrictive. They can provide just the right amount of support, at just the right t

Transcribed - Published: 4 April 2024

(Encore) Speed DWG: Dyeing To Be Dateable

In the first episode of our new microcast, Speed Dating While Gray, a matchmaker makes a provocative, off-topic comment about Laura’s gray hair.

Transcribed - Published: 28 March 2024

Location, Location, Location

Does the number 1 rule in real estate value also apply to finding new love? Hometown dating field reports are filed by listeners including Marina, in Denmark’s capital city; and relational coach Diana Lockett, in a ruggedly scenic part of Canada.

Transcribed - Published: 21 March 2024

Maybe I Do

Listener Stacy is mulling over a marriage proposal. History and tradition suggest that’s the ultimate romantic commitment expression. But at our age, does it make financial sense? For help answering that question, Laura calls on two experts: a financial planner, and a prenup attorney.

Transcribed - Published: 14 March 2024

Sex On My Mind

Maybe we’re doing it, maybe we’re not. Maybe we want to, maybe we don’t. We might be thinking about it … intimacy coach Anna Marti offers insights for all of us, plus Cate and other listeners share their concerns.

Transcribed - Published: 7 March 2024

Long Leap to Love

When it comes to finding love or making a commitment, is there ever an expiration date? Laura talks with Julie, who’s been on the dating market for almost a quarter-century. Then she checks in with Clyde and Trish, who’ve chosen the slow road despite instant chemistry.

Transcribed - Published: 29 February 2024

Revisiting That Other Reality Dating Show

What happens when a journalist covering the older-dating beat tries to get real about a TV show? Listeners weigh in with their opinions – about The Golden Bachelor and also, everything Laura said about it for Slate’s recap podcast.

Transcribed - Published: 22 February 2024

Dating in Real Life

Longtime dating coach Damona Hoffman offers practical and optimistic insights from her book, “F the Fairy Tale: Rewrite the Dating Myths and Live Your Own Love Story.” Plus, listeners share their true stories about the search for love.

Transcribed - Published: 15 February 2024

Trailer: Reintroducing Dating While Gray

With true stories and expert insights, host Laura Stassi continues her journalistic mission to uncover and share what it takes to make and keep new love connections in the later years of life.

Transcribed - Published: 8 February 2024

Encore: What (Some) Men Want

An online encounter has Laura wondering: When it comes to older heterosexual dating, are women trying to school men? Weighing in are widower Steve, a feminist who bristles at traditional advice; and Kevin, who’s still feeling the sting of the gray divorce his wife initiated.

Transcribed - Published: 25 January 2024

Encore: Love and Business

When couples mix business and pleasure, can both their romantic and work partnerships survive and thrive? Laura talks with “accidental CEO” Allison, and home-building entrepreneur Karen. This episode sponsored by Edgespace.

Transcribed - Published: 18 January 2024

Encore: More Dishing on Dating

With five committed relationships in 20 years, the apps are panning out for listener Jean. Plus, two former Dating While Gray guests randomly connect online and make a dinner date. Laura tags along and then uncovers what happened afterward. Was it a love hit … or a miss?

Transcribed - Published: 11 January 2024

Encore: Dishing on Dating

After counting up the romantic encounters she’s had this year, Laura asks older singles for their numbers. Tea spillers include Vinnie and Rachel; Kevin, who discovers three times is not the charm; and Allison, who widens her Zip code parameters.

Transcribed - Published: 4 January 2024

Encore: It’s 420 Somewhere

A dating site profile question leads Laura to explore cannabis use among older daters. Dosages, smoking vs. ingesting, medical and bedroom benefits … listeners weigh in with their cautionary tales, tips, and true stories.

Transcribed - Published: 28 December 2023

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