Dating and social skills podcasts worth listening to

Podcasts are an easy way to take in dating advice, because you can do it while you walk, lift or commute. The catch is that "dating podcast" covers very different things: long-form interview shows, coaching shows, women talking about what happens on their side, and plain social skills. Pick by what you're stuck on.

Everything below was checked in October 2026 against Apple Podcasts listings, official sites, Podnews or Wikipedia. Episode counts and schedules change, so treat them as a snapshot as of October 2026.

The Jordan Harbinger Show (Jordan Harbinger). Harbinger co-founded The Art of Charm podcast, hosted it for 11 years, and left in early 2018 to start this one, according to Wikipedia. Apple describes it as in-depth conversations with people at the top of their fields, turned into practical takeaways for work, life and relationships. It's listed as updated daily, with about 1,400 episodes. Start with: a Feedback Friday episode, where Gabriel Mizrahi (listed as co-host) joins Harbinger, or a guest episode on a skill you want, like conversation.

The Psychology of Your 20s (Jemma Sbeg, iHeartPodcasts). Sbeg explains the psychology behind experiences of your twenties, including dating, friendship, mental health, career anxiety and money, according to Podnews. The show publishes new episodes regularly, but sources disagree on the exact days, so check your podcast app. Start with: any episode whose title names something you're actually dealing with. They're built around one topic each.

Long-form interview shows

Modern Wisdom (Chris Williamson). Williamson is an English podcaster who has hosted the show since 2018. Wikipedia reports more than a billion downloads, and Apple lists about 1,200 episodes, updated weekly. It's long-form conversation with authors and researchers, with guests including Robert Greene, Jordan Peterson and David Goggins. Dating is one topic among many. Start with: the episodes on relationships and the sexes, such as "Why Men & Women Are Giving Up On Each Other" with Daniel Cox (#1166).

Coaching shows

The Gary Gunn Show (Gary Gunn). Gunn is a dating and self-confidence coach. Apple's description covers practical advice for men on approaching women, communication, dating and relationships, plus his private coaching methods. It's been running since 2018, is listed as updated twice a week, and had reached episode #610 in October 2026. Start with: the most recent numbered episodes, then pick by topic.

Love Life with Matthew Hussey (Matthew Hussey, with Audrey Hussey, Stephen Hussey and producer David). Apple describes it as a relationship and dating show covering relationships with others, with yourself and with life, mixing practical dating advice with personal reflection. It's listed from 2015 with about 1,000 episodes, and the description says new ones come out every Wednesday. Start with: an episode on a topic you're dealing with, such as ghosting or heartbreak. More on him in Matthew Hussey and what women are told about dating.

Shows hosted by women

Dateable (Julie Krafchick and Yue Xu). Part of the Frolic network. Apple describes real daters and experts discussing attachment styles, choosing a partner, healing from breakups and dating in your 30s and beyond, with new episodes on Wednesdays and listener questions on Sundays. It's listed from 2016 with 755 episodes. Start with: the Sunday listener-question episodes.

Where Should We Begin? with Esther Perel. Each episode is a recorded session in Perel's office with a real couple. Per the official site, the couples are anonymous and new episodes come out weekly, on Mondays. Start with: a session that matches a problem you've had.

Why Won't You Date Me? with Nicole Byer. A comedy show from Headgum where Byer talks about dating with comedians, experts and sometimes her exes. Apple lists 472 episodes since 2017, weekly on Fridays, with an Explicit label. Start with: an episode on a topic you're curious about, like "Dating a Short King" with Marcella Arguello.

Modern Love (Anna Martin, The New York Times). An adaptation of the Times' Modern Love column. The podcast debuted in January 2016, and Martin has hosted since 2022, according to Wikipedia. It publishes weekly. Start with: any episode that sounds like your situation, since each one is a single story.

How to choose

If you're stuck on	Try
Conversation and meeting people	The Jordan Harbinger Show
Approaching and texting, coached	The Gary Gunn Show
A host's different point of view	Dateable, Love Life
Hearing real couples talk	Where Should We Begin?
Big-picture ideas from authors and researchers	Modern Wisdom
Hearing other people's dating stories	Why Won't You Date Me?, Modern Love

These shows disagree with each other. That's fine. Hearing a coach say one thing and a couples session show another gives you more to work with than either alone. For books and video, see pickup and dating books worth reading and pickup and dating YouTube channels worth watching.

What to take from them

Pick two shows, not nine. One about social skills (Harbinger or Psychology of Your 20s) and one from a different point of view (Dateable or Perel). Give each three episodes before you decide.
Listen to the Feedback Friday and listener-question episodes first. Listener questions are often a close match for problems you might have.
Write down one line per episode. Not a summary, a single thing you'll try. "Ask a follow-up before I share my own story" counts.
Try it within 48 hours. Say the thing in an actual conversation: a coworker, a barista, someone at the climbing gym. If it feels stiff, change the wording and try again.
Cap it at two episodes a week. Listening feels like progress, but approaches and conversations are where you get better. A rule that helps: for every hour you listen, have one real conversation with someone new.
Notice where you disagree. If a host's advice feels wrong for you, that's information. Keep what fits how you actually talk.

Tracking what you try

If you use Run Game, the notes on a session are a good place for that one line per episode, next to what happened when you tried it. Field reports in the forum start from a short template: where, what happened, what worked, what you'd do differently. See how to write a field report.