Why Oh Why

Loose Ends Dec 26, 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, Bumble Mike, and Mona Chalabi. Then, does your host have a secret boyfriend? In a Twitter survey, 35% of our listeners thought this was a possibility. Plus, two great Panoply shows we think you'll adore. Subscribe to By the Book and Family Ghosts wherever you get your podcasts.

Say in touch! Follow @andreasilenzi on Twitter and Instagram.

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Just Another Sad Love Song Dec 17, 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. Eardrummings Vol. 19 by Schuyler. "Here's a playlist of songs that sort of put words/music to how I feel during my lowest lows. These sounds help me swim my way through that almost-drowning sensation and find my way back to a place that feels safer and clearer."

2. Songs Schuyler Might Like by Tom

3. Songs Tom Might Like by Schuyler

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Casual Dec 08, 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 Donaghue explains the value of a strong sexual connection in the early stages of dating. He's the author of "Sex Outside the Lines" and co-host of LoveLine with Amber Rose.

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Stage a Fight with Esther Perel Dec 01, 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 on Audible. She's also the author of "The State of Affairs: Rethinking Infidelity." Plus, our strangest Blind Skype Date yet,

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Find Your Single Ladies (Live in Chicago) Nov 23, 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 American Ninja Warrior find love the old fashioned way: with a game show. Find out how five single ladies from our Chicago audience fare when we ask them real questions from the 1960s TV show The Dating Game.

Ethan Swanson is on Instagram @ethanswanson.ninja, and he's a coach (alongside your host's brother!) for Ultimate Ninjas Chicago.

Thank You, MM.LaFleur

Today's show was made possible by MM.LaFleur, the women’s workwear brand whose mission is to take the work out of dressing for work. Each MM.LaFleur customer works one-on-one with an MM stylist, who helps her build her work wardrobe in a systematic, personalized way.

To try a Bento Box yourself, visit MMBento.com. Use code WHY at checkout and MM.LaFleur will donate 10 percent of profits to PAWS Chicago.

Thank You, The Fest

This episode was recorded live at Chicago Theatre Works, as part of The Fest, an annual festival of live podcasts, every fall in Chicago, curated by the Third Coast International Audio Festival.

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End of the World Sex Nov 17, 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 sex, politics and woke misogynists in the Trump era.

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Dating While Brian Nov 09, 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 episode came to us as a suggestion from Luke Terrell. (You might remember him from our LA show? He was the guy who made out with a girl on stage.) Luke is a filmmaker focused on telling stories about young adults with disabilities, and his latest project "Gabe" (with a few cameos from Brian!) is currently looking for distribution. To learn more about the film, visit thegabedoc.com or follow the film on Facebook.

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Ghosting Stories Oct 20, 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.

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Stop Dating Older Guys Oct 12, 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.

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Birth Control by Stapler Oct 05, 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.

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The Perfect Storm Sep 23, 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 he said yes.

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Puppies or Ice Cream? Sep 16, 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 suggest a few ideas that just might work for you. Helen is the host of the The Allusionist podcast, and we especially adore her episode about online dating profiles.

Plus, Mandy Len Catron helps us become better matchmakers. She's the author of the book How to Fall in Love with Anyone.

Wanna Be Set Up on a Blind Skype Date?

You don't even need to wear pants! Just fill out this Google form to be considered in our pool of singles or visit our website: whyohwhyradio.com.

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Leagues Over the Sea Sep 08, 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?

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My Friend the Human Shield Aug 29, 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 jumped into the fray, using his body to defend the man from kicks and punches. Letson is the host of Reveal from the Center for Investigative Reporting and PRX.

And for the Spiel, is “#whaboom” the worst of our culture today?

Today's show comes from Andrea's recent appearance guest-hosting Slate's The Gist podcast.

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A Man and a Woman Walk into a Bar Aug 13, 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-author of F*ck Love, who suggest dating like a headhunter. Then we'll hear from a range of writers including James Michael Sama ("Here’s Why Men Should Still Pay For Dates"), Elizabeth King ("Why A Woman Should Definitely Pay On The First Date") and Tiffanie Drayton ("Why I Refuse To Pay For Dates").

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One Short Episode Jul 29, 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 Through." She has also written about her relationship for the New York Times.

Our sponsors for this episode are Casper (code: WHY) and Squarespace (code: WHY). Go to casper.com/WHY or squarespace.com and use the promo code for special offers.

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Can You Fall in Love with Anyone? Jul 23, 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 Times, which was one of the top 5 stories the paper ran in 2015.

You can try “The 36 Questions That Lead to Love” by downloading this free New York Times app to your phone, tablet or other device.

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Game of Groans Jul 17, 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 Game of Thrones-themed pop-up bar in DC, and consulted an expert, Isaac Butler, to figure out how we should swipe on Thone-shots.

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Live at Bonobos - Making Out in LA Jul 13, 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 Exploder, West Wing Weekly) and Lindsey Mortensen (Larsen & Lund) tell us about their whirlwind bi-coastal courtship.

You can listen to "Accidents" by The One AM Radio again on their website.

To see photos from our live show, visit whyohwhyradio.com.

This live show was made possible by Bonobos. If you want to find clothing that will fit you better than you ever imagined, and get 20% off your first purchase, visit bonobos.com/whyohwhy.

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Dressing Room Confessionals Jul 09, 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 rooms.

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Live at Bonobos - Branching Out in Chicago Jun 30, 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 Podcast, Peter Kim (Second City, Seeso's Shrink) and Eunji Kim (Cards Against Humanity) help audience members re-vamp their Tinder profiles.

To see photos from our live show, visit whyohwhyradio.com.

Why Oh Why: Live At Bonobos! This summer we're taking over Bonobos Guideshops across the country for special live podcast tapings. These shows are all sold out! But even if you don't have a ticket, Why Oh Why subscribers will get to hear everything that goes down in special bonus episodes. Our LA episode comes out in two weeks.

This live show was made possible by Bonobos. If you want to find clothing that will fit you better than you ever imagined, and get 20% off your first purchase, visit bonobos.com/whyohwhy.

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Like a Virgin Jun 26, 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 late. We'll talk with a lovely member of the so-called "hook-up generation" next to a pool in Florida. What can her romantic resume tell us about the state of dating today?

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Data-ing Jun 15, 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 tell us more about what everyone's hiding, and how it all relates to our dating lives.

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Live at Bonobos - The Rules for Dating in NYC Jun 14, 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 performer Andy Beckerman help an audience member find love, and share how they found each other in the NYC improv scene.

To see photos from our live show, visit whyohwhyradio.com.

Why Oh Why: Live At Bonobos! This summer we're taking over Bonobos Guideshops across the country for special live podcast tapings. These shows are all sold out! But even if you don't have a ticket, Why Oh Why subscribers will get to hear everything that goes down in special bonus episodes. Our LA episode comes out in two weeks.

This live show was made possible by Bonobos. If you want to find clothing that will fit you better than you ever imagined, and get 20% off your first purchase, visit bonobos.com/whyohwhy.

Learn more about your ad choices. Visit megaphone.fm/adchoices

Why So Forlorn, OK Cupid? Jun 08, 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 Michael Bierut. They're the cofounders of Design Observer, and hosts of The Design of Business | The Business of Design and The Observatory podcasts. We're also joined by Teddy Blanks, a graphic designer and founder of design studio Chips. He makes the logo for our podcast.

To follow along with the corresponding visuals for our design discussion, visit whyohwhyradio.com.

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Deep in the Woods Jun 01, 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 first live radio experiments starring our hilarious pal Jim Behrle, and our even more hilarious relative Grandma Phyllis.

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Don't Listen If You're My Ex-Boyfriend May 05, 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 her sister, Elizabeth Craft.

Baldwin Way is an assistant professor at the Ohio State University. You can find his research study about acetaminophen dulling emotions here, and can read more about the connections between physical and emotional pain here. If you haven't read that Modern Love column, you can find that here.

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Hotter on Bumble, Part 2 Apr 21, 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 and teaches other people how to be engineers, too. He tweets: @reynaldadolphe

Chris Volinsky was part of the winning team for the Netflix Prize to develop a better recommender system. He's assistant vice president of big data research at AT&T, and he tweets: @statpumpkin

To discuss this week's episode, head to facebook.com/whyohwhyradio or tweet with #whyohwhy. You can find Andrea on Twitter as @andreasilenzi.

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Hotter on Bumble, Part 1 Apr 14, 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 episodes (#1, #13, #26), and our episode about The Bachelor (#23).

Valerie Woolard is a developer with Megaphone, the technology side of Panoply. She tweets: @valeriecodes

Satnam Narang works at Symantec, and has been following spam and bots on Tinder since 2013. He tweets: @satnam

To discuss this week's episode, head to facebook.com/whyohwhyradio or tweet with #whyohwhy. You can find Andrea on Twitter as @andreasilenzi.

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Muscle Thrasher Apr 07, 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 blind dates are full of awkward small talk), we've always wondered what became of our eligible bachelors and bachelorettes.

In this episode, hear about the dating life of Robynn Europe. What's it like to date while looking so outwardly strong?

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Aspiring Dads Focus Group Mar 31, 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 joined by this show's editor, and host of The Longest Shortest Time podcast Hillary Frank for a parent's perspective. You can subscribe to her show in iTunes, or wherever you find your podcasts.

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Your Best Foot Mar 24, 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.

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Tips from a Gentleman Mar 17, 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 of gold, or is there something darker at play? Would you take his dating advice seriously?

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As Seen on TV Mar 10, 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 facebook.com/whyohwhyradio or tweet with #whyohwhy. You can find Andrea on Twitter as @andreasilenzi.

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Going There Feb 25, 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 facebook.com/whyohwhyradio or tweet with #whyohwhy. You can find Andrea on Twitter as @andreasilenzi.

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One Date at a Time Feb 16, 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: whyohwhypodcast.com, and every week we send 10 new subscribers our latest Why Oh Why swag. To discuss this week's episode, head to facebook.com/whyohwhyradio or tweet with #whyohwhy.

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Do I Hate Men? Feb 09, 2017

Before listening to this week's show, we recommend starting out with our "Dudes in Bars" episode from last week.

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 talked to in bars around the country. And we ask men whether or not they're feminists. Turns out, it's not such an easy question to answer.

To discuss this week's episode, head to facebook.com/whyohwhyradio or tweet with #whyohwhy. You can find Andrea on Twitter as @andreasilenzi.

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Dudes in Bars on January 21, 2017 Feb 02, 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 facebook.com/whyohwhyradio or tweet with #whyohwhy. You can find Andrea on Twitter as @andreasilenzi. Did you hear we have a weekly newsletter with a weekly swag giveaway? You can sign up on our website: whyohwhy.sexy.

You can find Allie Hock's podcast Everything is Fine! here: etfshow.org. Alice Anderson's podcast Veneers is at veneerspodcast.com. And Selly Smith's Regular Black Radio can be found here: regularblackradio.com.

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What Ifs and Butts Jan 26, 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. Patricia Raymond, who performs musical parodies online as Ms. Butt Meddler.

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Alone Forever Jan 20, 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 to facebook.com/whyohwhyradio or tweet with #whyohwhy. You can find Andrea on Twitter as @andreasilenzi. Did you hear we have a weekly newsletter? You can sign up on our website: whyohwhypodcast.com

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Hacking the Uterus 2.0 Dec 22, 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 episode from Why Oh Why's years as a baby podcast. Travel back with us to January 2014, as your host prepares for her own IUD insertion.

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Single Straight Lady Focus Group Dec 20, 2016

For the first episode of this season, 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 finding a partner essential to our longterm happiness?

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Oblique Strategies Dec 06, 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 called "Messy" about the value of bringing intentional disorder into your world.

One of the many podcasters offering advice in this episode is Mike Pesca from Slate's The Gist. You can hear their full conversation on episode #606, "Mike Debates His Former Producer About Dating." Plus, Helen Zaltzman, of The Allusionist podcast, concocts a weird way to attract dates, and Daniel Lavery, from Slate's Dear Prudence podcast, might have the best advice of all.

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Listen to Your Heart Nov 29, 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 Tinder. Here to explain the art of sonic branding is Steve Milton, a founding partner at Listen, who helped craft the app's new signature sound.

Plus, in Trump's new America, our Facebook friends keep talking about getting an IUD. Why? We'll discuss the outlook for women's reproductive healthcare in the coming years with Slate's Christina Cauterucci.

Get Slate Plus:

Andrea was recently interviewed by Slate's Leon Neyfakh about her decision to bring her personal life back into this show. To read this interview, sign up for a free trial: slate.com/whyohwhyplus

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Separation of Church and Date Nov 22, 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 the Episcopal Church, and Nick Chiurazzi, a Pastor of Youth at Lower Manhattan Community Church.

Get Slate Plus:

Andrea was recently interviewed by Slate's Leon Neyfakh about her decision to bring her personal life back into this show. To read this interview, sign up for Slate Plus: slate.com/whyohwhyplus

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Just My Swipe Nov 17, 2016

This week, we're heading into the past, to a simpler time. When Why Oh Why re-launched 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-fashioned way: with a game show. Our staff swiped through Tinder to find contestants, and then Joanna put them to the test, asking many of the real questions from the 1960s show The Dating Game.

We also hear briefly from the folks at IMTOY about their new line of inspired vibrators. More info: http://imtoy.com/ProductZoo

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How Will I Know Nov 08, 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 and creator of the podcast The Longest Shortest Time.

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Dating with the Stars Oct 25, 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 anonymous Raya members teach us what it's like to swipe amongst John Mayer, Kelly Osbourne, Moby, Raven Symoné, Fred Durst and Sharon Stone. Is this the best place ever to find a boyfriend, or the absolute worst?

More info about today's show available on our website: badhombres.us

Get the newsletter: Once a week, the Why Oh Why team will send you episode extras, updates from favorite guests (like David #1), and our own personal recommendations. It’s also the best way to stay up-to-date on events and opportunities to participate in future episodes of the show. To sign up, click here.

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A Celebration of Awkwardness Oct 17, 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. You won't believe his trick for mellowing out on a first date.

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Hillary Clinton Sex Dream Oct 11, 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 played out through Sarah's art. Her portraits bring Hillary into a new light, showing us nude Hillary, butch Hillary, and even Hillary as James Buchanan. You can browse her portraits of Hillary on our website, whyohwhyradio.com, and follow her on Instagram as @hillaryporm_official.

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Can Meddling Help a First Date? Oct 03, 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 moment.

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Single Straight Guy Focus Group Sep 19, 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 philosophies—for better or worse.

If you like the show, be sure to tell your friends, lovers, exes, colleagues, and colleagues' exes to subscribe.

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