The Jesse & Anna Show Podcast

Jesse reveals the last time he thought about quitting his job! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Anna reveals what "level 3" has in store for Jesse this week in her goal to get Jesse a girlfriend! Plus, Jesse and Anna give out more compliments on a Monday and Anna forms a relationship with a fictional character! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Jesse doesn't usually feel guilty. But in this story, he does... and he didn't even do anything wrong! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Anna tells a story that she never thought she'd tell on the air.... Her most recent embarrassing moment, it's a gas! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

In today's show, Jesse failed on his level two dating mission, Anna talks about getting ripped off with her first-class ticket and we give out some more compliments! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Anna does a little self-reflection and talks about the rudest thing she does! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

We all did weird things as a kid to keep us entertained... find out what Jesse would do out in Iowa See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Jesse and Anna discuss kids using tablets with Jake, Jesse talks about a person on a dating app who found his address and expensive water bottles in Vegas! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Anna is excited to find out what Jesse thinks she's better at than him! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Briana thinks her electrician Derrick is hot and wants to ask him out! She has to confess she doesn't actually need hm to come to their scheduled appointment because it was only to see him again! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Anna talks about the struggles women have to face in everyday life that men don't! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

On today's show, Jesse and Anna discuss the coolest places they've taken a picture, Anna talks about her trip out west and we check in with Country Superstar, Riley Green! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Everyone seems to love this... except Anna! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

What is the most desperate thing that Jesse did to get a woman? Gotta listen to find out! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Jesse and Anna talk to Riley Green about all his success of late! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Anna's involvement in Jesse's dating life continues as AI creates a new bio for his dating profile! Plus, an update on Anna's vocal nodule, Nigel and some more advice from TikTok about Dinner Parties! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Jesse almost made this stupid decision back in the day! Find out what chaos he narrowly avoided! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Colin wants his sleep! He admits to his wife that every time she gets up to feed their 3-month-old, he's pretending to be asleep. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Has Anna ever hated a gift she was given and not told the person giving it to her? See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Anna has taken matters into her own hands to help Jesse get into a relationship, Jesse and Anna talk about things you shouldn't say to people and they give out some great compliments today! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Well, this is doozy. Took quite the turn but find out about Anna's most awkward encounter with an "ex". See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

What's the latest thing Jesse will judge you for? Find out in this edition of the Truth Jar! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Jesse and Anna have a special surprise for Jake that ends in tears. Plus, Anna checks in with her dad, Ron, before Father's Day and Jesse gives an update on his dating ultimatum Anna gave him. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Jesse's question today is a juicy one... is Anna Jesse's best friend? See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Anna feels guilty about a lot, but she refuses to feel guilty about THIS! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .