3 dates later podcast by Emily and Kyle

Last Updated: June 20, 2026

About:

Everything seemed to point in the direction of positive dating potential when Emily and Kyle match on a dating app…  both in their 40s and “dating intentionally”, they have three dates together over a week that seemed to get better and better- and both agreed they wanted a fourth- but they never got there.  Instead of just parting ways, their curiosity led them to a decision  to dissect every step and misstep along the way in an effort to figure out if the outcome was inevitable or if they could have done things differently to make it to the fourth date. 

With the hope of possibly doing it better with the next match, they go through topics that most singles have to navigate: dating with kids, red flags, “rules” of dating, sexual chemistry, safety, personal history & traumas, ghosting, and many others that two people getting to know each other rarely speak openly about once it ends: and nothing is off the table or too vulnerable.  


S1 Episode 9 - This is The End and Endings Matter
Published:

Season 1 wraps with some tears and revelations about how things could be done differently the next time… and where things go from here- or if it’s time to walk away. 

S1 Episode 8 - We Both Made Mistakes
Published:

Even though Emily and Kyle continued constant contact, by Sunday night things have taken a drastic turn that changes things for both of them and neither hold back their opinions or emotions while discussing why. 

S1 Episode 7 - Was it Actually The Kiss of Death?
Published:
After the anticlimactic ending to their third date Kyle and Emily have a few days apart and realize that maybe there are some disconnections previously unknown. 
S1 Episode 6 - She Ends Up in a Cage in His Basement???
Published:

Emily and Kyle go through some of the conversations that seemed harmless at the time  but turned out to be a bit more revealing. 

S1 Episode 5 - My Place or Yours?
Published:

After a  few hours at the mall,  Kyle ends up at Emily’s house to “Netflix and chill”… but an unexpected ending may be more telling than either of them realized. 

S1 Episode 4 - We should pump the brakes - and meet up
Published:

What is intended to be an  easy going meet up turns into engagement ring shopping and interrogations. 

S1 Episode 1 - Normally I Would Not Still Be Talking to You
Published:

Kyle and Emily sit down and backtrack through their initial interactions to see if there are signs that can start pointing them to why date 4 never happened. Discussing the app profiles, red flags and other roadblocks that pop up when dating in your 40s.

S1 Episode 2 - I Don't Know if This is Going to End Well For Me...
Published:

The first date happens.. Did all signs point to go,  or were they ignoring red flags? Emily and Kyle meet and decide to put it all out on the table.

S1 Episode 3 - Apparently We Can’t Joke
Published:

Some texting over communication between leads to some turmoil.  Between future faking conversations and texts taken out of context more red flags may pop up.

Copyright © 2026 PodcastSearch.org All Rights Reserved.