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After seeing this question and having an epiphany, I created a custom list with a Calendar view. This custom list uses a content type I created called "Time Off Request." Here is what the form looks like:

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What I want to do is send an email to the person chosen in the "Supervisor" dropdown. The email would contain the information from the form request. Here's the mockup:

enter image description here

So ideally, the selected supervisor gets the email, clicks the link the approve the new item, and moves on. My question: How can I achieve this functionality? I have a feeling I need to use approval workflows, but I'm not sure where to configure how the approver gets appointed and notified.

EDIT: I know C# but I have never used it in conjunction with Sharepoint 2010. I'm definitely willing to employ it as a solution.

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