Waupun Man Sentenced to 5 Years for Sexually Assaulting Teenage Fiancée

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A 34-year-old Waupun man, Alan Shierling Jr., has been sentenced to 5 years in prison for sexually assaulting his 15-year-old fiancée. Shierling pleaded no contest to one count of second-degree sexual assault of a child, with three additional charges dismissed as part of a plea deal. He will also be required to register as a sex offender upon his release.

Why it matters

This case highlights the serious issue of adults engaging in sexual relationships with minors, which is considered statutory rape and a serious crime. It also raises concerns about the potential for predatory behavior and grooming of vulnerable teenagers by older individuals.

The details

The investigation into Shierling began in January 2025 after concerned citizens reported an "inappropriate relationship" between the 33-year-old and the 15-year-old victim. Authorities found evidence that Shierling had recently proposed to the underage girl, and that the two had engaged in sexual intercourse on numerous occasions. Shierling was arrested during a traffic stop in Rubicon, where the victim was present in the vehicle with him.

• The investigation into Shierling began in January 2025.
• Shierling was arrested in February 2025 during a traffic stop in Rubicon.

What’s next

Shierling will serve 5 years in prison and 15 years of extended supervision following his release. He will also be required to register as a sex offender.