The Quest (Episode 2)

If we've learned anything this year, it's that life is precious. And while endings are tough, they're also a good reminder to make the most of the time we have.John Cotrocois learned this when he went on a date with his ex-boyfriend's ex-boyfriend. Michelle Goodman survived it (and much more) when she became a widow at 50. And Natalie decides it's time to leave town, and has to break the news to Jack the Chef.

Sometimes, we have to be forced to admit something isn't working before we take the steps to figure out how to make it work. In 12-step programs, they call this hitting rock bottom. Which is an idea that might also apply to the global pandemic our world is facing right now...

Ever struggled to fit in? Or fought to stand out? Natalie shares how her Lebanese heritage impacted her views on marriage, beauty and belonging. Jasmina Najjar talks about being single in Beirut, a culture obsessed with marriage and couplehood. And as a 6'3 woman, Janna Klostermann turned her sexuality into a joke - until her body made her take things a lot more seriously.

Sex and love addiction affects so many, but there's so much shame around it. Mandy Stadtmiller, author of "Unwifeable", shares her story about sex and love addiction, and talks about trauma, divorce, and finding her soulmate where she least expected to. And Natalie opens up about her own love addiction and recovery, and her uncertainties about Jack the Chef.

Sometimes, it takes being single to figure out who we really - REALLY - are. Mike Sagun tried to "pray the gay away" - and was shunned by his family and his faith when he came out. No'a Bat Miri tells us about being Orthodox Jewish by choice, and single by choice. Courtenay Stickels explores all the women she left behind and found again when she came back to herself. And Natalie explores - and owns - losing herself when she's in a relationship.

Baggage: we’ve all got it. How can we use it for good, instead of letting it weigh us down? After his first big love ended in bigger betrayal, Shane’s unusual journey of singlehood took him from his darkest hour to his true potential. Faith’s marriage to a sex addict made her a better person – and a better parent. And Natalie sleeps with Jack the Chef… with worrying consequences.

Christos meets Amy Schumer at a hotel spa and prepares to ask her out. (Yes, the Amy Schumer.) We also talk to Sarah, who, in a very single phase of her life, spends some quality time with someone who can fly. And as Natalie prepares to go on a third date with Jack the Chef, she finds herself lost in fantasy... until she meets a very unexpected reality.

Dating can shed a lot of light onto the way we see ourselves, and the world. After a brutal divorce and a run of disappointing relationships, Cheryl shares the one surprisingly simple lesson that turned her luck around. On the advice of her therapist, Natalie dives into the world of "dating badly", and is forced to examine some of her own boundary issues. She has a worryingly good date with a dude named Jack, she and Christos swap war stories ... and strategy.

Lots of us have a thing about trying to fit into molds of who we think we're supposed be. This week's episode: being uncool (in the best way possible). We also cover breakups, bullying, near-death experiences, grief and spiritual journeys... in the best way possible.

Join Natalie Karneef as she gets divorced, dissects Tinder, and delves into why our culture values couplehood over singledom.