EPISODE · Feb 12, 2026 · 25 MIN
Why Is Portland So Bad at First Dates?
from City Cast Portland · host City Cast
With Valentine’s Day just days away, it's a good time to remember just how complicated dating can feel in Portland. Today, comedian Jay Flewelling joins us to talk about the state of love in Portland: what’s broken, what’s funny, and what might actually work. He’s also bringing dating horror stories from Mack Lee and Aleah Liebenau, co-hosts of Heart Throb, a comedy show that turns Portland dating chaos into a good time. Catch Heart Throb: The Dream Date Show on Saturday, Feb. 14 at Kickstand Comedy. Become a member of City Cast Portland today! Get all the details and sign up here. Who would you like to hear on City Cast Portland? Shoot us an email at [email protected], or leave us a voicemail at 503-208-5448. Want more Portland news? Then make sure to sign up for our morning newsletter and be sure to follow us on Instagram. Looking to advertise on City Cast Portland? Check out our options for podcast and newsletter ads at citycast.fm/advertise. Learn more about the sponsors of this February 12th episode Portland Art Museum D'Amore Law Pivot Portland
What this episode covers
With Valentine’s Day just days away, it's a good time to remember just how complicated dating can feel in Portland. Today, comedian Jay Flewelling joins us to talk about the state of love in Portland: what’s broken, what’s funny, and what might actually work. He’s also bringing dating horror stories from Mack Lee and Aleah Liebenau, co-hosts of Heart Throb, a comedy show that turns Portland dating chaos into a good time. Catch Heart Throb: The Dream Date Show on Saturday, Feb. 14 at Kickstand Comedy. Become a member of City Cast Portland today! Get all the details and sign up here. Who would you like to hear on City Cast Portland? Shoot us an email at [email protected], or leave us a voicemail at 503-208-5448. Want more Portland news? Then make sure to sign up for our morning newsletter and be sure to follow us on Instagram. Looking to advertise on City Cast Portland? Check out our options for podcast and newsletter ads at citycast.fm/advertise. Learn more about the sponsors of this February 12th episode Portland Art Museum D'Amore Law Pivot Portland
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Why Is Portland So Bad at First Dates?
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