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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Tips from a Gentleman

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 often blurring the lines between memoir, documentary, and fiction.

Personal Journals

Society & Culture

History

Philosophy

Places & Travel

Comedy

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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Loose Ends

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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Just Another Sad Love Song

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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Casual

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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Stage a Fight with Esther Perel

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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Tips from a Gentleman

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