Ashlee Simpson and Pete Wentz: Double Date Night

Now that she’s engaged (and possibly pregnant) Ashlee Simpson has a whole new world of things to consider. And who better than a fellow celebrity to help guide her along the way!

The “Little Miss Obsessive” singer and fiancé Pete Wentz were spotted on their way to a double dinner date with new parents Nicole Richie and Joel Madden last night.

And they were both beaming, as well they should be as a newly-betrothed couple. Ashlee rocked a black sweater/black skirt/black shoes combo while her Fall Out Boy beau opted for a seafoam green and black hoodie with a pair of black jeans.

Simpson’s new album is scheduled to drop next Tuesday, April 22nd. And “Bittersweet World” sounds like a bold new direction for Ashlee, kind of like her life as of late.

Gossip Girls

Enjoy the pictures of Ashlee and Pete out in the Big Apple last night (April 16).