Six Podcasts for Lonely Hearts

No V-Day plans? Spend quality time with these love lessons and confessions.

By Shannon Rupp 12 Feb 2016 |

Shannon Rupp is a contributing editor at The Tyee and our podcast reviewer. Know of a show you think she should hear? Mention it in the comments section or tweet her @shannonrupp.

Come Sunday, Feb. 14 you may well long to have someone whisper sweet nothings in your ear, which is where some podcasts could come in very handy if you're single.

Perhaps because the medium lends itself to intimacy and confessions, many podcasts talk about love, in all its weird variety, and have a particular affinity for stories of love-gone-wrong.

What could be a better listening choice for lonely hearts on the Hallmark holiday devoted to romance?

So, while the rest of the world gears up to sell chocolate, jewels, and roses, you can enjoy a day of feeling smug and above-it-all. And then take advantage of those half-priced flower sales on the 15th.

Many of us are inclined to make cynical remarks about the commercialism of VD. (And was there ever a more appropriate shorthand for a holiday?) But trust me when I say that you will have heretofore unimagined respect for those enterprising florists after hearing Planet Money's 2015 episode 603, "A Rose On Any Other Day."

It documents the elaborate dance that South American rose growers and local flower sellers have to do so that we can all have perfectly opened bouquets of long-stemmed red roses on the day.

Suddenly that $100 for a dozen roses in mid-winter seems like a bargain.

Hurt and horror

If you thrill to the awkward charm of rom-coms you'll no doubt be delighted by a new podcast from the New York Times featuring famous actors reading stories from their long-running Modern Love series. They dig up old essays, and then host Meghna Chakrabarti interviews the author to get an update. There are only a handful of podcasts in the archive, but they're all worth a listen.

And don't miss Judd Apatow -- who directed Knocked Up and The 40-Year-Old Virgin -- reading an essay by an awkward, neurotic guy, who could be an Apatow character. He ends up in the emergency room on a first date. And then a follow-up interview tells us what happens after an incident that looks more like a horror movie than a rom-com.

You think your break-ups have been bad? You can't match Lea Thau, the woman with the distinctive, haunting voice behind the Strangers podcast. When you hear people talking about the special intimacy of the podcast genre, they're talking about the sort of pieces that the Peabody Award-winning Thau does.

She's a wonderful storyteller who has a knack for getting people talking about the private, revealing details of their lives. But nothing is quite so riveting as the four-part story she told about her own life.

The "Love Hurts" series began when Thau decided to explore why she had been single for four years after being dumped, in a spectacular fashion, by her fiancé. She was in her late 30s and seven months pregnant when she discovered he was having an affair. The details are horrifying. (And the fact that a few hundred thousand people get to hear about what he did suggests that podcasting might be the best revenge.)

But Thau doesn't stop with that confessional. Over four episodes and more than a year, she documents her dating life. And when it goes off the rails, she interviews the men who rejected her.

What, exactly, is wrong with her she asks? Her questions are brave. And cringeworthy. And it makes for compelling radio. Will she ever sort it out? I won't tell. But it's worth listening for the more than three hours it will take for you to find out.

Sweet talk

The Agony Aunt -- advice for the lovelorn -- is one of journalism's oldest and most popular columns, stretching back to the 18th century and it's a natural fit for podcasting's up-close-and-personal style.

So it wasn't surprising to see one of the format's recent stars, Dear Sugar, take her hit column from the literary magazine Rumpus to a podcast. Sugar's real name is Cheryl Strayed, and she's the author of Wild, the memoir that inspired the 2014 Reese Witherspoon film. For the audio version, she's joined by co-host Steve Almond, who is also fiction writer, and an equally sensitive soul.

Together I'm sure they give out sound enough advice, but of course that's not why we follow advice columns. We follow them to criticize their views.

It's probably fair to say that I am absolutely the wrong audience for Dear Sugar, who I consider far too inclined to sympathize with her whiny audience. So I have a tendency to talk back to the podcast. To snort. To roll my eyes. To tell them to grown a spine. Or get a pair. Or generally shape up and stop whinging!

That, my friends, is the fun of it. Perhaps this is the secret of success for all advice columns? The feeling that, no matter what advice they offer, we could do it better.

Just in time for Valentine, Dear Sugar has a three-part series on finding "The One" -- that stock character from romance novels and rom-coms. Apparently, the Sugars' audience of women in their mid-30s is getting nervous about their prospects on the marriage-mart. Some are wondering if they should "settle" as some of the self-help books suggest. (That's a cue for my 10-minute rant on how people really ought to stop treating other people as commodities.)

In the first episode they interview Millennial wunderkind Lena Dunham, who writes the TV show Girls about 20-somethings failing at life and love. So she's bound to know something about love crises involving the soon-to-be middle aged.

The Sugars' brand of handwringing does something for me that the editors of my youth said was the secret of good newspaper column-writing: you outrage the reader in a way that makes her want to come back and argue with you again tomorrow. To be honest, I never really believed them, since I'm inclined to ignore people I think are wrong, wrong, wrong.

But there's something about the Dear Sugar brand of wrongness that keeps me coming back for more. I'm guessing it's because the podcast, which is well done, also gives me a glimpse of a world that I don't see anywhere else.

Savage advice

That's certainly the appeal of Dan Savage's advice column, which can only be improved by putting Mr. Savage on podcast -- the Savage Lovecast. Online he's free to be even more candid than he is in print. (Yes, he will often leave you slack-jawed.)

I have a weakness for Savage's heady mix of politics and blunt talk. No kid gloves here for his advice-seekers. And he never fails to call out the self-deluding in ways that have me doubled over laughing. I've been a fan since he launched the call-in show in 2006.

Not only will he brighten any lonely Valentine's Day with a dose of his sharp wit, his podcast is probably the most soothing one on this list. It's quite comforting to listen to his callers and their strange romantic conundrums and realize that, as long as you remain single, you will never have to deal with people like this. Start at his latest show, and work back. It's all good.

But in the tales of the romantically challenged, leave it to This American Life to dig up a story about the world's most passive-aggressive couple. They're making tentative steps toward getting married after 13 years together, all the while breaking up in inches. It's funny. And sad. And the sort of story that could happen only in this era. It's called "The Best Laid Plans" and it's found in a round-up episode of romantic stories, none of which seem to end well.

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