Is Chicago my forever home? 

This has been a question that has been on my mind for sometime now. I have wanted to have a discussion on this topic, but didn't know what the conversation would look like and honestly I've been scared to have it too. I sit down with life long family friend, Jack Brynes to discuss Chicago's problems, our love for this great city and what can we do to turn it around. Truth is, we have a long way to go, but hopefully this is a start.

This week Jenna chats with her former classmate, Vanity Walsh, as she opens up about being in an abusive relationship, losing her fiancé, being shot at, and getting bit in the face by a dog. Besides all the lows Vanity has faces, she still find the goods and highs in life. Get ready to be inspired and gain a new perspective in this incredible conversation.

Not the original episode Jenna had in mind, but when your life is in a state of disarray, it will naturally lead to a different topic. In this week's episode Jenna discuss how she's learning to surrender to the higher plan, easier said than done and something Jenna's still figuring out.

We're picking up right where we left off! Jenna, Terri & Benji answer questions, and Terri flips the script and makes Jenna answer some rapid fire questions.

A drunken conversation in the outfield at a White Sox on a Sunday Funday turned into today's episode! Jenna sits down with her cousin, Terri Shinnick and bar regular, Benji Woods to discuss what dating looks like in your 20s, 30s & 40s. Sit back, relax and grab a drink! You're gonna want one for this.

Nothing will ever be “normal” again!

After going out the first weekend that Chicago reopened Jenna realized that as much as we want to say everything is back to normal, NOTHING is! This week Jenna shares 3 important things to know as you reenter society.

Jenna shares a drink with The Draft Network CEO, Paige Dimakos. The two discuss running towards adversity and being okay with embracing it, how treating everyone the same got Paige in the Arizona Coyotes owners box for life, how at the start of Paige’s career there were not many supportive women in the industry, and an ode to the professor at Nebraska that knew Paige had “it.”

Jenna’s drinking some Uncle Nearest Whiskey with Victoria Butler, Master Blender behind the award winning and fastest growing spirit ever. Nathan “Nearest” Green, who was enslaved until 1865, and the man that taught Jack Daniels how to make whiskey is the great-great-grandfather of Butler. Whiskey may run in her blood, but the journey to becoming a Master Blender is anything, but ordinary. Listen to hear how Butler didn’t realize her family history was unique, and what she would say to Nearest if she could.

Jenna shares a drink with professional hockey player, Chelsey Goldberg to discuss what the PWHPA is working towards, why Chelsey feels it's the right time to move back home, to embrace the adversity that's throw your way, and how small our problems are in the grand scheme of things.

TRIGGER WARNING: Miscarriage/ Infant Loss

Jenna sits down with Ally Redig of Athlete Relations to discuss her business, the care she has for her clients that shines through in her work and the inspiration behind her “Woman in Sports” hoodie. Ally also opens up about her miscarriage, why she wanted to talk about it publicly and her advice on what to say to someone that has miscarried.