MissJudged Podcast

AI vs. The Matchmaker - Which Is Best For You!? w/ @Annamorgenstern

MissJudged Podcast Season 2 Episode 5

Buckle up, lovebugs—this one’s a ride.
Dating coach and professional matchmaker Anna Morgenstern (@Annamorgenstern) joins Alyssa on the MissJudged Podcast to spill the messy, hilarious, and sometimes heartbreaking truth about modern dating. From ghosting to catfishing, we’re exposing why swiping culture has us all exhausted—and whether matchmaking is the real cure to dating app burnout.

Anna also shares her wild personal love story—reconnecting with her now-husband years after buying a Coachella ticket off Craigslist (yes, really). Together, we dig into the differences between algorithmic app matches vs. curated human matchmaking, how too much “choice” leads to dating paralysis, and why real chemistry can’t be coded.

In this episode, you’ll hear:

  • Anna’s journey from dating coach to full-time matchmaker
  • The untold story of meeting her husband through Craigslist + Hinge
  • Alyssa’s WORST matchmaker experiences (they’re cringe)
  • Why dating apps are full of filters, catfish, and false hope
  • The shocking mistakes most singles make when searching for love
  • Game time: Algorithm vs. Matchmaker—who wins?
  • How AI is reshaping the future of love and relationships

If you’re single, swiping, or just dating-curious, this episode will have you laughing, nodding, and maybe rethinking your entire Hinge profile.

Support the show

Like what you hear? Don’t forget to like, subscribe, and tell a friend to help spread the word! The more, the merrier, right?

Listen/ Watch to MissJudged Podcast:

Stay in the loop and follow us on

Instagram: @missjudgedpodcast

TikTok: @missjudgedpodcast

Hit play and join the conversation— can't wait to have you along for the ride!