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Love In The Time Of Overalls

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Illustration by Tara Jacoby

Sometimes you’ve just gotta make a terrible choice and ride it out. There’s no other way to learn. People will try to warn you, but you will relegate all your buddies and relatives to the role of Cassandra. You’ll tell yourself they just don’t understand as you get back together with an ex, or buy a charming lemon of a car, or agree to take a position described as 30 percent hustle, 40 percent grit and 25 percent heart (I'm sure the rest is mostly empty calories). I once took a job as a volunteer editor at a small press in the hopes that it might turn into a paid gig someday; I was convinced of the legitimacy of the enterprise because the founder bought me business cards. I know better now, but I didn’t then, and so perhaps the experience was a gift. 

Romance is a perfect medium for ignoring other people’s sage advice. This week we bring you the story of Emily, a talented teenage singer-songwriter who falls in love with another young musician, Sasha. Is it a bad idea to share a dorm room with your girlfriend? How about signing up for all the same classes? Lending out your signature outfit to a new friend? Probably every reasonable person in the world would say yes to all these question, but that’s not enough to stop Emily. 

This week our guest is Gabby Windey! Gabby Windey is a TV personality you may recognize from The Bachelor, The Bachelorette, and Dancing with the Stars. Now she hosts a podcast called Long Winded

Gabby brought us a tantalizing story about a pop star with a homemade calendar of pictures of Gabby’s girlfriend. Then Kelsey told Gabby the story of Emily, Sasha, young love, love songs, young love songs, and uncannily flattering tie-dye overalls. 

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