On today's episode, Joss and Jen are joined by Stephanie O'Mahoney, a Wealth Advisor from Wealthsimple. Stephanie takes Jen and Joss through Wealthsimple's five simple steps to start investing and the emotional aspect of investing your money.

Joss and Jen bring on their assistant producer, Yolanda, to talk all things back to school. They reminisce on their elementary school days and give advice to those in college, especially those going in person for the first time.

Sam Diamond is the CEO of Bird&Be, a company that creates prenatals to optimize your fertility outcomes. Dr. Dan Nayot is one of Canada's top endocronologists and fertility specialists. Together, they discuss all things fertility, common questions, normalizing the conversation around it, and common infertility cases.

Joss and Jen discuss unpopular relationship opinions. Is long distance easy with the right person? Are love languages real? Is love a choice or a feeling? Is there such thing as a honeymoon phase? Can you make someone change? Listen to hear their takes and follow us on Instagram to share your own.

Ashley is a fashion and lifestyle blogger based out of LA. She talks about her start as an influencer and gives advice to those starting out. Ashley touches on authenticity on social media in regards to brand partnerships and the influencer lifestyle. Lastly, she touches on how social media detox works when social media is your job.

Joss and Jen reflect on friendships – how and why it's changed as they've gotten older. They give advice on how to make friends as an adult, and how to deal with friendship fallouts. They talk about what they value in friends and why it's ok to somtimes let a friend go.

Christine is an Asian-American actress best known for playing Angela in Tigertail and Emma on Dave. She talks about her start in acting, the progression of the Asian character in media, and the current roles she's playing – an upcoming rom com and the comedy series Dave.

Joss and Jen talk about their complicated relationships with food, and how that relationship has changed over time. They go from hard topics such as disordered eating, gut issues, and hormonal acne, to a deep hatred of vegan cheese?

Zander is a digital product designer, and CEO and founder of Memorisely, an online platform that provides live UX/UI design bootcamps. He explains what a digital product designer is and tells the story of how a surfing accident kickstarted his career in ed tech. He gives his perspective on starting a company and how Memorisely has always been community focused.

Joss and Jen discuss all things freelancing, from how to become one to all the implications of that lifestyle. They each touch on their own experience freelancing: how they started, and why they do it. They give advice on time management, explaining how they juggle freelancing, free time, and a full-time job.