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If I Were You

Tune in every Monday to If I Were You as Jake Hurwitz and Amir Blumenfeld offer advice in areas they're qualified to talk about. Also in areas they're not qualified to talk about. Email them with your own sticky situations and they’ll find the solution: IfIWereYouShow@gmail.com.

Weekly hand curated podcast episodes for learning

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The best episodes ranked using user listens.

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100: Family Fiction (with Ben Schwartz and Thomas Middleditch!)

Ben Schwartz AND Thomas Middleditch join us on our 100th episode! They advise, they sing, and they... get real.This episode is brought to you by Stamps.com and Squarespace.com!

50mins

8 Sep 2014

Rank #1

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387: Prison (w/Middleditch and Schwartz!)

Friends and comedians Thomas Middleditch and Ben Schwartz join us live from Thalia Hall in Chicago to discuss foreskin, new pants, and who is 58 years old.Thanks to everybody who came out to HeadGum Live last weekend!

1hr 14mins

17 Jun 2019

Rank #2

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127: Missing Dad (with Patrick Cassels!)

Our friend Pat Cassels joins us to discuss family dinners and very long distance relationships.This episode is brought to you by MottAndBow.com, SquareSpace.com, TheBouqs.com, and TaxAct.com!

1hr

15 Jan 2015

Rank #3

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137: Shower Sex (w/ Lil Dicky!)

Rapper Lil Dicky joins us to discuss masturbation, basketball, and getting older.This episode is brought to you by NatureBox, Audible, and Prosper.com!

1hr 1min

2 Mar 2015

Rank #4

Most Popular Podcasts

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409: Secret Santa (w/Thomas Middleditch!)

Comedian, friend, and lover Thomas Middleditch is in the studio to discuss moving to Australia, the Super Flu, and the greatest gift of all: Sand.For more IF I WERE YOU check out our Patreon.com/JA

51mins

18 Nov 2019

Rank #5

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Yes Dude (w/Ben Schwartz!)

Comedian/Friend/Lover Ben Schwartz joins us on this milestone episode to discuss DM's, Snapchat, and sitcoms.This episode is brought to you by Ring.com, BlueApron.com, and MeUndies.com!

58mins

15 Feb 2016

Rank #6

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300: A Celebration (w/Ben Schwartz!)

Friend, comedian, lover Ben Schwartz joins us to celebrate our 300th episode by discussing chipmunks, how to be funny, and his new book!

1hr

6 Nov 2017

Rank #7

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75: Harry Potter (with Dave Rosenberg)

Our boy Dave Rosenberg joins us to discuss breaking up, strip clubs, and tattoos.This episode is brought to you by NatureBox.com! Delicious, nutritious snacks delivered TO YOU. Use our coupon code for 50% off your first box: http://bit.ly/1idZxFp

45mins

5 May 2014

Rank #8

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119: The Wolf

In this episode we discuss good hobbies and bad friends.This episode is brought to you by Casper.com and DraftKings.com

43mins

8 Dec 2014

Rank #9

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71: Sim Cheating (with Thomas Middleditch)

Silicon Valley's Thomas Middleditch joins us to discuss mustaches, break-ups, and virtual world problems.This episode is brought to you by NatureBox! Delicious, nutritious snacks delivered to your door. Use promo code "ifiwereyou" for 50% off your first box! http://bit.ly/1idZxFp

56mins

7 Apr 2014

Rank #10

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222: Baton (w/Bo Burnham!)

Writer/Performer/Peeler Bo Burnham in the house to discuss rich kids, close friends, and his Netflix Comedy Special "Make Happy."This episode is brought to you by Squarespace, TrunkClub, and HeadSpace!

57mins

27 Jun 2016

Rank #11

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141: Chivalry (w/Ben Schwartz!)

Comedian/Actor/Friend Ben Schwartz joins us to discuss courtship and comedy.This episode is brought to you by RetailMeNot.com, TrunkClub.com, and MeUndies.com!

46mins

16 Mar 2015

Rank #12

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89: One Less Problem (with Ben Schwartz)

Ben Schwartz joins us to discuss... whatever the hell he wants.This episode is brought to you by Squarespace.com and AVG Cleaner.

58mins

14 Jul 2014

Rank #13

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326: Strip Clubs (w/Thomas Middleditch live in Vancouver!)

Comedian and Friend Thomas Middleditch joins us to discuss STD's, DND, and Canadian Folk Hero Stan Rogers. Recorded Live at the Vogue Theater as part of Just For Laughs: Vancouver!

56mins

26 Apr 2018

Rank #14

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98: Underwear (with Thomas Middleditch)

Friend and star of "Silicon Valley" Thomas Middleditch joins us to discuss technology, fidelity, and stealing underwear.This episode is brought to you by Stamps.com, SlugBooks.com, and MeUndies.com!

1hr 7mins

25 Aug 2014

Rank #15

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414: Amir on NADDPod

Special Holiday episode this week -- it's Amir's debut on Jake's Dungeons and Dragons podcast. And no, you don't have to know anything about Dungeons and Dragons to enjoy the show! So... enjoy the show!

1hr 47mins

23 Dec 2019

Rank #16

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345: Jake and Jill's Insane Wedding (w/Jillian Vogel!)

In this episode Jillian Vogel joins us to recap perhaps the most eventful wedding weekend of all time. Note: This is a true story. Also worth mentioning: BUCKETS! Amir's new NBA Podcast. Subscribe wherever you're listening to this.

59mins

27 Aug 2018

Rank #17

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111: Clam Dip (with Dave Rosenberg!)

Our special friend Dave Rosenberg joins us to discuss working out, jealousy, and his grandma's secret recipe.This episode is brought to you by Squarespace.com and DollarShaveClub.com!

49mins

23 Oct 2014

Rank #18

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412: Pissing in a Sink

In this episode we discuss the pros and cons of bath-houses as a means of relaxation, the trials and tribulations of growing your hair out, and lastly, whether or not you can drink your own pee pee.For more IF I WERE YOU check out bonus video episodes on Patreon.com/JA.

39mins

9 Dec 2019

Rank #19

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407: The Best Coffee

In this episode we discuss flat whites, bathroom locks, and why breaking up is easy to do.For more IF I WERE YOU check out our Patreon.com/JA for weekly bonus video episodes!

45mins

4 Nov 2019

Rank #20