The entire show Sex and the City was built around a central part of single female friendships - the need to talk through our dating challenges and stories with our friends. But what happens when you need comfort or empathy and instead you get hit with judgment or even criticism (!)? Jen and Audrey share recent examples of “tough love” from friends that crossed some boundaries.

Everyone these days seems to know if they have an avoidant or anxious attachment style. Jen and Audrey discuss their styles and how their understanding of attachment theory influences how they date - or not. With one who leans avoidant and one who leans anxious, the two compare their different styles and how they’ve navigated dating men who fall into different categories.

No podcast about dating in your 40s would be complete without a discussion around the challenges of dating as a single parent. Listen in to hear Jen reflect on how dating as a single mom requires managing a lot of logistics and navigating a minefield of emotions and challenging conversations.

Jen and Audrey dive into the challenges of building relationships in your 40s and 50s. Ever feel like you’re lugging around a suitcase full of emotional baggage and the Ghosts of Traumas Past? Listen in to hear how they are dealing with exes, kids, and the complexities of midlife while trying to date and find love!

In this episode of "40's in the City," Jen and Audrey discuss their shifting perspectives on masculinity in the dating scene. Living in New York City in their 40s, they grapple with the contrast between their past desires for dominant, masculine men and their current attraction to men who are more kind and giving. Join them as they discuss if their preferences have changed or if their definition of masculinity has changed.

Jen unknowingly matches with and has a date with a service sub. Instead of digging her heels into her desire for a dominant, assertive man, she decides to explore and ends up learning interesting things about herself in the process. Jen and Audrey also discuss the dating app Feeld and various kink parties that happen around NYC.

Jen realizes that if she doesn’t want a serious relationship, why not open up the age range on her app and explore connections with much younger men during her holiday break from parenting. Listen in to hear how that went and how Audrey and Jen view major age differences and if they matter.

Audrey and Jen break down their experiences with dating apps from Bumble, Feeld, Hinge, Tinder, and the League. Are matchmaking services worthwhile? They weigh out the pros and cons and discuss what goes into a profile.

Word on the street is that NYC is the worst place in the country for single women to date, and the best for men. Is that true? Jen and Audrey chat about whether they agree and what makes dating here so different, challenging or better.

Jen and Audrey compare and discuss recent first dates. What makes a good first date? How long does it usually take a guy to propose to meet IRL? Does the location matter? Should it be just drinks or dinner? They chat about what went well and what didn’t.