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For this week’s Slate Plus bonus segment, the hosts discuss several additional conundrums. Slate Plus members get an ad-free version of this podcast with bonus segments. Visit slate.com/gabfestplus and try it free for two weeks.

On this week’s Slate Political Gabfest, Emily Bazelon, John Dickerson, and David Plotz—live at Park West in Chicago—discuss (and occasionally attempt to dodge) tough political, philosophical, and ethical questions about sending kids to private school, keeping secrets from spouses, and whether they wish they’d had more sex in their 20s. Amy Dickinson, author of the popular Ask Amy advice column, joins to help tackle some of the conundrums.

Here are some of the questions discussed during the show, as well as the names of some of the questioners:

• Imagine that the night your current significant other proposed to you, they told you that they have a 3-by-3 metal box that you can never open, and you can never know what is inside. Would you continue with the relationship? –Ben Heilveil
• Would you rather have a grand, fabulous job that’s beyond your capacity, but worry everyday about being debunked as a fraud? Or would you rather have a small, demeaning job that’s well within your scope of capability that allows you to make a meaningful contribution to the world? –Rachel
• Is it more right to tell underprivileged young people that they can be whatever they want to be? Or is it more right to tell them that society is unfair and they’re getting the short end of the stick?
• Is it wrong to take advantage of your privilege? When is it wrong to take advantage of privilege? –David
• Would you rather have $10,000 today or $20,000 a year from now?
• Would you give up your smartphone for five extra years of life? –John
• Do you think you can be an ethical and sincere advocate for the public school system and send your kids to private school? –Alex Madison
• Close friend is having a Native American–themed kids birthday party. Is it OK to do it? Should you call out your neighbor on this?
• What piece of advice would you give to your 22-year-old self? –Phil Goldstein
• Is there such a thing as a truly evil person? –Sean
• What state would you get rid of? –David
• Would you use the opposite sex’s bathroom where there is no line, or would you wait in line at your own?
• In an argument between a child and a parent, does the other parent have an obligation to side with their spouse even if they believe the kid? –Cecilia

Amy chatters about a shout out from Ashton Kutcher.

John chatters about an experience with his son modeled off of an exercise in Joshua Foer’s Moonwalking With Einstein: The Art and Science of Remembering Everything.

Emily chatters about connecting with her kids.

David chatters about singing Rodgers and Hammerstein’s “You’ll Never Walk Alone” at Liverpool Football Stadium.

Topic ideas for next week? You can tweet suggestions, links, and questions to @SlateGabfest.

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The email address for the Political Gabfest is gabfest@slate.com. (Email may be quoted by name unless the writer stipulates otherwise.)

Podcast production by Mike Vuolo. Links compiled by Maxwell Tani.