Sharon is 38 and never been kissed. This, as she acknowledges, is “a bit weird.” As a nurse who loves ballroom dancing, Sharon is smart, funny, and attractive. At the same time, she’s deeply religious and has been waiting so long for the perfect man she worries that she’ll never find “The One.” In this episode of How To!, we bring in one of New York City’s finest matchmakers, Lisa Clampitt, for some tough love. Lisa believes Sharon has a lot going for her, but in order to find her first kiss she needs to go on a lot more second dates. This is no fairytale, but sometimes you have to kiss a few frogs before you find your prince.

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When Hema first realized she was gay a few years ago after immigrating to the U.S., she knew she had to tell her mom. But the conversation didn’t go well. Hema’s mom lives in India and is convinced being gay is a Western phenomenon. So how does Hema help her mom accept her for who she is? In this episode of How To!, we bring in Sonali Gulati, a professor, filmmaker and queer rights activist who made a documentary about the parents of LGBTQ people in India. Drawing from her own personal experience, Sonali helps Hema figure out the best way to frame the conversation with her mom. One tip? Speak your parents’ language to explain how your life fits their definition of success. 

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Anthony is that rarest of things in American politics—a swing voter who is up for grabs in 2020. Caught between his Republican voting history and his current dislike of President Trump, Anthony is now registered as an Independent. But does he follow his head or his heart? In this episode of How To!, we bring in veteran political advisors David Axelrod, chief strategist for Barack Obama’s presidential campaigns, and Mike Murphy, a Republican consultant, who co-host the podcast Hacks on Tap. David and Mike discuss how to weigh ideology vs. electability and rank the issues that really matter. Can their advice help Anthony—and all of us—make sure our vote counts?

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Lorenzo is a dental student with big dreams—of becoming a rock star. Lorenzo plays a mean guitar at open mic night, but there’s one thing holding him back: He doesn’t know how to write his own songs. In this episode of How To!, we bring in master songwriter Ben Folds, former frontman of Ben Folds Five, and author of A Dream About Lightning Bugs: A Life of Music and Cheap Lessons. Many of those lessons are about how anyone can unlock their creativity. Ben breaks down his own music, and tinkers with Lorenzo’s attempt at writing a break-up song. He tells him to embrace cliché, then slip in something unexpected. Also, switch the first lyric with the second. Will it work?

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Shannon runs a nonprofit in Aspen, Colorado — a place filled with wealthy donors, but also stiff competition. With nearly 500 nonprofits vying for money, how does Shannon help her organization stick out? Some of the best advice may come from an unlikely source: con artists. In this episode of How To!, Maria Konnikova, author of The Confidence Game, shares con artists’ surprisingly similar tricks of the trade: Identify your mark, listen carefully, then tell them a story they want to hear. Can Shannon use these same techniques for a good cause? 

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The coronavirus outbreak in China is causing panic worldwide. The World Health Organization has declared it a global health emergency and all we hear about are doubling infection rates, massive quarantines, and drugstores running out of masks. In this episode of How To!, we ask Dr. Elisabeth Rosenthal, former New York Times reporter and author of An American Sickness, how she and her family survived the previous SARS epidemic in Beijing. We also revisit our conversation with Dr. Tom Inglesby, Director of the Johns Hopkins Center for Health Security, about what to do—and what not to do—if the coronavirus becomes a full-blown pandemic and spreads to where you live. 

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Andy would do anything for his girlfriend Cassie. Well, almost anything. As Cassie looks to move away for vet school, Andy has to decide if he’s going with her, leaving his job, family and friends, and two bands behind in Austin, TX. In this episode of How To!, we bring in Rachel Hollis, author of Girl, Wash Your Face and her husband Dave, author of Get Out of Your Own Way. The Hollises have a lot of experience navigating this question, because for most of their marriage, Dave’s job as a Disney executive took priority—until he quit to support Rachel’s career. He tells Andy the first step in making this decision is to treat it like a choice, not an obligation. 

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Jason has been addicted to meth for the past 15 years, which is not uncommon in his small Illinois town. Every time Jason stopped using he would relapse, until last year when the state took custody of his two kids. Since then he’s sobered up, but is worried about making it last. In this episode of How To!, we bring in Fred Muench, a clinical psychologist and recovering heroin addict who is now the president of Center on Addiction/Partnership for Drug-Free Kids. Muench knows how hard it is to beat the stigma of addiction. To convince people he’s changed, Fred says, Jason must first convince himself.

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Joe Loya robbed more than 30 banks during an 18-month span before going to jail. Charles wants to rob one bank on a Saturday afternoon, and get away scot-free. Can Joe teach Charles the tricks of the trade? Or will he shatter his dreams, and a few stereotypes along the way? Also, is it a good idea to carry a microphone while attempting a robbery?

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This episode originally aired July 30, 2019.

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Once upon a time, Ashley met a man and fell in love. Now, she’s ready to get down on one knee and pop the question. But with so few women proposing to men, she’s not sure how to go about it. In this episode of How To!, we bring in Caroline Kitchener, staff writer for The Washington Post’s The Lily, to share her own unlikely proposal story. She tells Ashley not to worry about stealing a man’s thunder. As for planning the perfect engagement, forget flash mobs and diamond rings — Kitchener says a relationship contract is the first step for a successful marriage.

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