We're baaaaaaccckkkk!! Thanks for sticking with us while we took a little hiatus. This week Kimmie Caruba and Shannon Whelan catch you up on what's been happening behind the scenes, reminisce thanks to the debut of Disney+ (complete with all of our favorite shows from our childhood) and dive into mind games. 

Shouldn't This Be Easier

Episode 8: Disney+ and Thrill

Episode 7: Happy Halloween!!

Everyone always talks about how to make yourself feel better after a romantic breakup -- ice cream, sad movies, going out with your friends... But what happens when the person you're breaking up with is actually your friend? The one that you tell all of your secrets to and the one that has been there for you during said romantic breakups? This week, Kimmie Caruba & Shannon Whelan share stories of broken friendships, the unnecessary feelings of shame and how best to move on and heal. 

Episode 6: Friendship Breakups

This week, Shannon returns from a bachelorette party getaway in Austin, TX with wildly contrasting stories to the bachelorette weekend Kimmie attended in Arizona a few months ago. From the hours of planning, to the thousands of dollars spent, and every bride meltdown in between, Kimmie Caruba and Shannon Whelan don't hold back when it comes to the drunken dramatic details of bachelorette parties. 

Episode 5: Stories from the Bachelorette Battlefield

Listen, dealing with other people in the world can already be a challenge. So why do some people have to make it SO much harder to do?! Especially when you're TRYING to be nice to them -- aka DATE them?!?! This week, Kimmie Caruba and Shannon Whelan share a few of those messages they wish they had never gotten, as well as some situations that just get under your skin, no matter what you do.

Episode 4: Why Are You So Rude

On this week’s episode Kimmie Caruba and Shannon Whelan talk about ending things... but were things ever really started? From the guilt that comes with ending things, to the back and forth of, "Did I do the right thing?!" and all of the feelings in between, you can find it all in this week's episode of Shouldn't This Be Easier. Oh, they also get into the PROPER way (apparently) to break things off. 

Episode 3: Breaking Up With Someone You're Not Actually Dating

This week, Kimmie Caruba & Shannon Whelan show life's messy side as they open up about the things that they're bad at, but seemingly no one else is... or you shouldn't be bad at... either way, the 'bad' is on full display. 

Episode 2: How Can You Be Bad At That?

They're awkward, they're nerve-wracking, they're exciting but sometimes (mostly?) just downright BAD. For their first episode, Kimmie Caruba & Shannon Whelan share their personal experiences with going on that first date with someone new. *first date horror stories included* More on the dating statistics mentioned in this episode.

Episode 1: First Dates

Shouldn't This Be Easier is a brutally honest catalogue of the real-life stories of two twenty-somethings living in Chicago. From dating & relationships, to job loss & family drama, nothing is off-limits. Listen weekly as Kimmie Caruba & Shannon Whelan talk of life's ugliest, messiest, and most beautiful moments while trying to make things just a little bit easier for us all.

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Shouldn't This Be Easier

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