Jessica Simpson's New Man: John Mayer

Jessica Simpson's New Man: John Mayer
Mayer and Simpson in 2005
Lester Cohen/WireImage

updated 08/30/2006 AT 09:40 AM EDT

originally published 08/29/2006 AT 06:45 PM EDT

Jessica Simpson is embarking on a not-so-public affair – with singer-songwriter John Mayer, PEOPLE has confirmed.

"She's tiptoeing back into the dating world," a source tells PEOPLE. "It's the first stage. She's never been happier."

Mayer, 28, began a co-headlining tour with Sheryl Crow on Aug. 24, and Simpson, 26, is expected to attend his concert in Jones Beach, N.Y., on Wednesday night.

Simpson is currently in New York promoting her new album, A Public Affair, which was released Tuesday – although a bruised vocal cord has quashed any planned performances. (She did stop by MTV's TRL Tuesday and is set to appear on Today on Friday.)

Similarly, Mayer had to cancel his Hartford, Conn., appearance with Crow on Saturday due to laryngitis, the Associated Press reported.

The two singers have known each other for several years and last year both attended Clive Davis's pre-Grammys party in Beverly Hills.

Although Simpson has been linked to Jared Leto and her Employee of the Month costar and Teen Choice Awards cohost Dane Cook, Simpson has not officially dated anyone since her November 2005 separation from Nick Lachey.

For more on this story, pick up the new issue of PEOPLE, on newsstands Friday.

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