Relationships & Love

Why Oh Why

Andrea Silenzi / Panoply

+30 FANS
Named a best new podcast of 2016 by The New York Times, NPR, Huffington Post and iTunes. Andrea Silenzi speaks with friends, experts, and guys in bars about where love, dating and sex meets technology. The show tells the stories about relationships o...Show More
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#48: The Perfect Storm

39:37 | Sep 23rd, 2017

While Hurricane Irma sped towards Miami, Emily decided to ask a guy from Bumble if he wanted to evacuate with her as a 3rd date. Her family has a home in the woods of North Carolina, and they'd be out of town that weekend. Here's what happened after ...Show More
#47: Puppies or Ice Cream?

49:17 | Sep 16th, 2017

Helen Zaltzman has a way with words, which is why we're putting her to work solving one of the trickiest parts of online dating—composing your opening messages. Some lines can break the ice, while others just throw more ice into the void. We'll sugge...Show More
#35: Data-ing

34:06 | Jun 15th, 2017

The persona we create online or on apps isn't very representative of what's going in our lives. So we brought in Seth Stephens-Davidowitz, author of "Everybody Lies: Big Data, New Data, and What the Internet Can Tell Us About Who We Really Are" to te...Show More
#6: Dating with the Stars

29:02 | Oct 25th, 2016

This week on Why Oh Why, we attempt to plant one lucky listener inside a private dating app for celebrities, Founded by a PR executive in 2015, Raya targets "users in creative industries," which is a coded way of saying, "famous people." Plus, two an...Show More
Meet a new podcast: Bad With Money with Gaby Dunn

52:20 | Jun 20th, 2018

Friends, it’s been a while.  I stopped by the Panoply studios to chat with our old Why Oh Why producer, Lindsey. Somehow, she's been able to fill the hole left by Why Oh Why by working on another show called Bad With Money with Gaby Dunn, and I think...Show More
Meet a new podcast: By The Book

41:53 | Feb 8th, 2018

Oh, hey there! I'm back again to introduce you to another great show from my friends at Panoply: By The Book. Their latest episode is all about The Five Love Languages, and I think you'll really get a kick out of how the hosts, Kristen and Jolenta be...Show More
Meet a new podcast: When Meghan Met Harry

25:13 | Jan 10th, 2018

Hey guys. Remember me? You know, Andrea Silenzi? It hasn't been that long. I popped back in the studio for a little update, and because Why Oh Why's producer, Lindsey, had some news to tell me. And no, this is not a new episode of Why Oh Why. It's an...Show More
#59: Loose Ends

40:20 | Dec 26th, 2017

We have news. Starting in 2018, we're taking a break from making Why Oh Why. While we can't predict the future, let's call it a break not a breakup.For this special episode, we'll hear from a wide range of past guests including David #1, Randy, Bumbl...Show More
#58: Just Another Sad Love Song

53:18 | Dec 17th, 2017

This summer, Schuyler shared a playlist of songs that have helped her cope with depression and anxiety. It moved a lot of people in her life to reach out, including Tom. For all the feels, check out the playlists discussed in this week's episode:1. E...Show More
#57: Casual

42:00 | Dec 8th, 2017

After you've developed an allergy to casual sex, is there a cure? We talk with comedy writer and performer Matteson Perry about keeping things casual. He's the author of "Available: A Memoir of Heartbreak, Hookups, Love and Brunch." Plus, Dr. Chris D...Show More
#56: Stage a Fight with Esther Perel

58:04 | Dec 1st, 2017

Esther Perel has ideas for how to humor yourself on your first dates using a bit of role play. She's the host of the Audible original podcast "Where Should We Begin." You can hear Season 1 of the show on Apple Podcasts, and Season 2 is now available ...Show More
#55: Live in Chicago - Find Your Single Ladies

36:21 | Nov 23rd, 2017

Live from Chicago Theater Works, our show begins with the love story. Hear how a first date turned into a meaningful relationship for six single women. This story came to us after Lisette's brilliant Twitter thread went viral. Plus, we help an Americ...Show More
Panoply Fall 2017 Trailer

03:33 | Nov 20th, 2017

We’re thrilled to present Panoply’s Fall 2017 lineup of shows. They include the satirical self-improvement show “Dexter Guff is Smarter Than You (And You Can Be Too),” the creepy paranormal series “Haunted,” “Family Ghosts,” in which people play dete...Show More
#54: End of the World Sex

45:29 | Nov 17th, 2017

On election night last November, the world shifted beneath our feet... but what was going on our bedrooms? Nona Willis Aronowitz is a features editor at Splinter and writes a newsletter called "Fucking Through the Apocalypse." She joins us to discuss...Show More
#53: Dating While Brian

46:57 | Nov 9th, 2017

Brian has Muscular Dystrophy and gets around in a wheelchair, but that doesn't mean he won't make out with your girlfriend when you're not looking. On today's show, Brian tells his friend Luke what it's like for him to date with a disability.This epi...Show More
#52: Horrible Anonymous

40:37 | Oct 27th, 2017

You know that hit podcast where a comedian talks with an anonymous person for an hour, no holds barred? We love that show! That's why we wanted to try our own version. What could possibly go wrong...Wanna Be Set Up on a Blind Skype Date?We're matchin...Show More
#51: Ghosting Stories

43:56 | Oct 20th, 2017

Ghosting has been called the millennial way of breaking up, but that doesn't make the phenomenon any less haunting for its victims. Just in time for Halloween, we present a collection of ghosting stories from listeners across the country.Wanna Be Set...Show More
#50: Stop Dating Older Guys

42:29 | Oct 12th, 2017

The age gap between men and women in heterosexual dating has become a fact of life in the 21st century. The Guardian’s Mona Chalabi suggests it’s time for that to change. Read her op-ed "I Want My 2.3 Bonus Years" in the New York Times.Wanna Be Set U...Show More
#49: Birth Control by Stapler

37:32 | Oct 5th, 2017

The arm implant, known as Nexplanon, is a birth control option that's slightly more effective than the IUD, and less painful to insert. Why aren't we all using it? Why Oh Why's Lindsey Kratochwill investigates. Wanna Be Set Up on a Blind Skype Date?W...Show More
#46: Leagues Over the Sea

27:04 | Sep 8th, 2017

This week, with Bumble Mike in tow, we set sail on a singles mixer, organized by The League. Is finding a date while stuck on a boat easier than swiping through the apps? And more importantly, who's your favorite yacht rock artist?Our sponsors for th...Show More
#45: My Friend the Human Shield

30:43 | Aug 29th, 2017

In this episode, we talk to a human shield and a human billboard. First, Al Letson was just trying to cover a demonstration—an anti-hate rally in Berkeley. When he saw a group of balaclava-clad men descend on an apparent right-wing agitator, he jumpe...Show More
#44: Going Out with Randy

27:00 | Aug 21st, 2017

Can flirting with your problematic friend help you date better in the wild? Our regular guest, Randy, stops by to help your host cure a bad case of first date burnout.Our sponsors for this episode are ThirdLove and Winc. Go to or tr...Show More
#43: A Man and a Woman Walk into a Bar

28:51 | Aug 13th, 2017

Today on the show, we’re finally tackling THE QUESTION we're asked the most frequently as a podcast about dating: "Who should pay for the drink on a first date?"Join us for a Tour De Advice for straight daters, starting with Sarah Bennett, the co-aut...Show More
#42: One Short Episode

21:37 | Jul 29th, 2017

When determining your criteria for a date, how much should height matter? We'll talk to one woman who has always known exactly what she's looking for in a partner. Anna Goldfarb is a journalist and author of the book "Clearly I Didn't Think This Thro...Show More
#41: Can You Fall in Love with Anyone?

38:56 | Jul 23rd, 2017

If you can fall in love with anyone, how do you choose well? Mandy Len Catron offers an answer. She's the author of the book How to Fall in Love with Anyone. She also wrote the Modern Love essay "To Fall in Love with Anyone, Do This" for The New York...Show More
#40: Game of Groans

33:07 | Jul 17th, 2017

Many fans of the HBO show Game of Thrones use photos of themselves sitting proudly atop an Iron Throne replica for their online dating profile pictures. But what's the symbolic meaning of the sword chair? We sent a correspondent to the heart of it: a...Show More
#39: Live at Bonobos - Making Out in LA

42:44 | Jul 13th, 2017

What's the biggest difference between dating in LA and dating in NYC? Our running theory: there's more making out, usually in or near cars. We'll offer advice for Angelenos with help from TV kissing expert, Erica Rose. Then, Hrishikesh Hirway (Song E...Show More
#38: Dressing Room Confessionals

37:33 | Jul 9th, 2017

This summer, we went on the road to tape live shows at Bonobos Guideshops in NYC, Chicago, and LA. And in true Why Oh Why fashion, we asked our audience to tell us their deepest secrets in makeshift confessional booths set up inside the dressing room...Show More
#37: Live at Bonobos - Branching Out in Chicago

32:38 | Jun 30th, 2017

Sometimes in order to find love, you have to figure out what you love to do. We begin by exploring our Chicago roots, and a story of how Andrea's mom answered the question, "What do you like to do for fun?" Then comedians and co-hosts of the Ajumma P...Show More
#36: Like a Virgin

31:13 | Jun 26th, 2017

Are millennials spending too much time behind their screens and not enough time in the back seats of cars? Recent studies show that the generational cohorts born in the 1980's and 1990's are starting their sex lives later than Gen X'ers did. Twice as...Show More
#34: Live at Bonobos - The Rules for Dating in NYC

40:49 | Jun 14th, 2017

We begin with a story: The tale of your host's earliest ancestor’s dating life, and the love life of a more recent relative, Grandma Phyllis. Then comedian and writer Naomi Ekperigin (Broad City, Difficult People) and her “Jew Boo” writer and perform...Show More
#33: Why So Forlorn, OK Cupid?

54:12 | Jun 8th, 2017

Does OK Cupid's app icon tell a larger narrative of chaos and distress? Let's use the logo design of popular dating apps to explore the state of the companies and the substance of their products. In doing so, we're joined by Jessica Helfand and Micha...Show More
#32: Deep in the Woods

28:48 | Jun 1st, 2017

Over at Why Oh Why HQ, we're planning quite the event for our first live show with Bonobos. And it got us thinking about the joy of crafting a live show and the fun of experimenting with the medium. Today, we'll listen back to one of this podcast's f...Show More
#31: Daddy Randy

28:06 | May 13th, 2017

The other day, Randy called to say he was outside Panoply studios. Didn't we get his fax messages? Hear why our show's favorite regular guest is happier than ever.Why Oh Why: Live At Bonobos!Join our show as we take over Bonobos Guideshops across the...Show More
#30: Don't Listen If You're My Ex-Boyfriend

35:08 | May 5th, 2017

How do you even begin to deal with heart break? Your host weighs the advice.We'll speak with Olga Pronin, the marketing manager at Wham-O. Dr. Fred Nour is a neuroscientist and wrote the book True Love. Gretchen Rubin hosts the Happier podcast with h...Show More
#29: Hotter on Bumble, Part 2

39:07 | Apr 21st, 2017

If our potential matches on Bumble feel hotter than other apps, who's making that decision? What does this mean for us normals?Reynald Adolphe caught our eye with his blog post: "Is Bumble's Algorithm Filtering Ugly People?" He is a software engineer...Show More
#28: Hotter on Bumble, Part 1

30:47 | Apr 14th, 2017

Bumble is held up as Silicon Valley's gift to single women. Finally, a dating app made with us in mind. But after you download the app and start swiping, does it live up to the reputation?In this episode, you heard clips from all our focus group epis...Show More
#27: Muscle Thrasher

39:55 | Apr 7th, 2017

In June 2013, your host and friends independently piloted a podcast idea called "Like Like." The concept involved setting up blind dates and recording them with wireless microphones. While we never completed a full episode of the show (it turns out b...Show More
#26: Aspiring Dads Focus Group

34:01 | Mar 31st, 2017

In which six single guys split between D.C. and Brooklyn studios share their plans for the future—down to the baby names. For listeners who aren't accustomed to hearing straight men talk about these things, queue the softcore porno music.Plus, we're ...Show More
#25: Your Best Foot

20:02 | Mar 24th, 2017

What do you do when you meet someone who doesn't meet your most essential criteria? Why Oh Why explores how turning thirty can change your dating life for the better.#TryPod:All this month, we’re asking you to tell a friend about a podcast they’ll lo...Show More
#24: Tips from a Gentleman

25:34 | Mar 17th, 2017

Jim's a 40-something guy who lives in Florida and exclusively dates strippers. What can he teach your host about improving her dating life in NYC?Tell Us:What do you make of Jim? Is he a real world Richard Gere seeking his own stripper with a heart o...Show More
#23: As Seen on TV

24:29 | Mar 10th, 2017

In a time when dating feels so broken, could The Bachelor be a reasonable last resort? What does a reality show get right?To discuss this week's episode and this month's #trypod campaign, head to or tweet with #whyohwhy. Yo...Show More
#8: How Will I Know (Welcome, Planet Money Fans!)

18:32 | Mar 2nd, 2017

The wonderful team at NPR's Planet Money just rebroadcast an episode that changed the life of your host. To welcome any new listeners into our show, here's the classic episode that Robert Smith recommended. Hope you enjoy.Old listeners, thank you for...Show More
#22: Going There

33:41 | Feb 25th, 2017

Today's episode is basically StoryCorps, but between total strangers in the back of a bar with the potential of sex later.Have you ever had a meaningful interaction with a stranger? To discuss this week's episode, head to o...Show More
#21: One Date at a Time

31:02 | Feb 16th, 2017

Think about it: The de facto first date invitation tends to be "let's get a drink." What's a single person to do when they don't imbibe?Did you hear we have a weekly newsletter? You can sign up on our website:, and every week we send 10...Show More
#20: Do I Hate Men?

20:59 | Feb 9th, 2017

Before listening to this week's show, we recommend starting out with our "Dudes in Bars" episode from last week. It's #19.For this week's show, we go back to the day of the Women's March, back to our army of lady interviewers and the dudes they talke...Show More
#19: Dudes in Bars on January 21, 2017

27:17 | Feb 2nd, 2017

How do we date men in a time when our rights are under attack? We sent 10 ladies into bars across the country on the day of the historic Women's March.To discuss this week's episode, head to or tweet with #whyohwhy. You can...Show More
#18: What Ifs and Butts

27:44 | Jan 26th, 2017

Is Uber the new Tinder? A lesson in how to shoot your shot when life sends you a cute driver. You can find Kelli on Twitter @KelliAmirah, and see her GIF-filled story here. Then, for the bottom half of our episode, a user's guide to your butt with Dr...Show More
#17: Alone Forever

22:22 | Jan 20th, 2017

What's going on with you romantically? Nothing? Our guest Aimée Lutkin says that's okay.You can read her Jezebel piece here, follow her on Twitter @alutkin, and read more about her #onTinderatTinder project here. To discuss this week's episode, head ...Show More
#16: Randy's Mema Died

25:14 | Jan 13th, 2017

This week on the show, our regular guest Randy finally goes off the deep end. Will your host dive in after him? Yes, it's a real website: To discuss this week's episode, head to or tweet with #whyohwh...Show More
#15: The Quiznos Guy

25:25 | Jan 6th, 2017

When your host first met Randy, it was the opposite of a meet-cute. We'll revisit the phone call that kicked off years of quasi-friendship.To discuss this week's episode, head to or tweet with #whyohwhy. You can find Randy ...Show More
#14: Hacking the Uterus 2.0

50:10 | Dec 22nd, 2016

The inexpensive reproductive healthcare coverage offered by the Affordable Care Act may soon be a distant memory. On today's show, we speak with a woman fresh off her own IUD insertion procedure to see how she's adjusting. Then, we revisit a classic ...Show More
#13: Single Straight Lady Focus Group

28:17 | Dec 20th, 2016

Back in episode #1, we welcomed 10 dudes into the studio to shout about their dating lives. This week, our latest focus group invites 14 single ladies in New York and D.C. to chat about the many thrills and face palms that come with dating men. Is fi...Show More
#12: Oblique Strategies

25:00 | Dec 6th, 2016

Single? Chances are, someone who is decidedly not single has given you advice lately. This week, Andrea asks economist and journalist Tim Harford to vet the various dating advice she's heard from friends and fellow podcasters. Tim has a new book out ...Show More
#11: Listen to Your Heart

20:51 | Nov 29th, 2016

When your host became newly single, she was shocked to discover that Tinder had made a drastic change as well. Like when silent films turned into talkies, though way less culturally significant, there is now a distinct sound when two people match on ...Show More
#10: Separation of Church and Date

27:39 | Nov 22nd, 2016

We ask a group of Christian ministers about what it's like to date when your other big relationship in life is with God. Our panel includes Amy Norton, a recent graduate from Harvard Divinity School, Cara Rockhill, an ordained Transitional Deacon in ...Show More
#9: Just My Swipe

33:46 | Nov 17th, 2016

This week, we're heading into the past, to a simpler time. When Why Oh Why re-launched on Panoply in the fall, we celebrated with our own special live show at the Kraine Theater in New York City. Andrea helped her friend Joanna find love the old-fash...Show More
#8: How Will I Know

25:26 | Nov 8th, 2016

This week on Why Oh Why, a look back at the role this show has played in your host's personal life. Travel through the past three years as Andrea talks to her editor, Hillary Frank, about what’s going on in her relationship. Hillary Frank is the host...Show More
#7: Too Old for Meet Cute

27:21 | Nov 1st, 2016

This week on Why Oh Why, Andrea’s friend Joanna tells the story of a truly horrible first date. It’s one of those dates that makes the other people at the bar uncomfortable—or grateful they’re not in her shoes. Joanna learns an important lesson that ...Show More
#5: A Celebration of Awkwardness

28:52 | Oct 17th, 2016

At the end of Episode #3, a surprise ending left us all cringing from head to toe. As an antidote, this week we welcome David back into the studio to share his side of the story. Plus, we head back to Bushwick to get a drink with that sexy Irish guy....Show More
#4: Hillary Clinton Sex Dream

17:10 | Oct 11th, 2016

This week, a love story that takes place in the mind of a mathematician-turned-artist. Sarah Sole began her unique obsession with Hillary Clinton in 2007, after a vivid sexual dream. It was the beginning of an imaginary, sexual relationship that play...Show More
#3: Can Meddling Help a First Date?

29:17 | Oct 3rd, 2016

This week on Why Oh Why, Kate and David go on a first date at a bar in Brooklyn. You might remember these two from the focus group episode--David is the guy who asked Kate out at the end. And just for you, dear listeners, Andrea recorded every single...Show More
#2: Randy's First Kiss

23:30 | Sep 26th, 2016

Remember Randy from last week's focus group? He told us why he's not on any of the dating apps, and how he meets women at Club Seacrets in Ocean City, Maryland. In this episode, we'll hear what made his first kiss unforgettable.If you like our show, ...Show More
#1: Single Straight Guy Focus Group

19:12 | Sep 19th, 2016

In this debut episode, Andrea finds out what's been going on in the dating world. As her guide: a focus group of ten single, straight guys split between D.C. and Brooklyn studios. With some liquid lubrication, the guys share their own dating philosop...Show More

01:28 | Sep 12th, 2016

Your host was hoping to play highlights from the new show, but found something better instead. Why Oh Why returns on Monday, September 19th.Learn more about your ad choices. Visit