Daily Insomnia Episode 369 - The Boyfriend Experience

In this episode, the cocktail of the night was the classic Mojito, and the boys were joined by their Venezuelan brother and Chicago comic Christian Henningsmeyer. As always, the Daily Insomnia crew hypes up their guy before diving into the wild world of the Chicago dating scene. From women’s endless lists of icks, to how both sides view what makes a date “bad,” to the truth that some women have no game, nothing is off limits. The conversation gets even spicier with talk of escort pricing in Chicago, the boys’ own kinks and search histories, and plenty more chaos along the way.

You can listen to Daily Insomnia Episode 369 - The Boyfriend Experience online on Radio and Podcast. Open the player on this page to stream the available audio.

Daily Insomnia Episode 369 - The Boyfriend Experience is an episode from Daily Insomnia Podcast by Daily Insomnia.

This episode is 64:46 long.

This episode was published on Oct 2, 2025.

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