First shots of Ashlee Simpson and Bronx after breakup with Vincent Piazza out and about with a mystery male in NYC on November 28, 2012. Credit: Jackson Lee / Splash News

Ashlee Simpson doesn't look too heartbroken over her recent breakup.

One day after Us Weekly broke the news of her split with Vincent Piazza, the "Bat for a Heart" singer stepped out for the first time in New York City Nov. 28 -- the same day Us exclusively reported the news of her sister Jessica Simpson's second pregnancy.

Wearing burgundy jeans, leopard print sneakers, a knit beanie, an Anita Ko rose gold and pave diamond arrow necklace and a fur-lined coat, the single star, 28, sipped a coffee and guided her 4-year-old son Bronx (with ex-husband Pete Wentz) through the Big Apple with the help of a hunky male pal. The blond little boy held hands with both his mom and her handsome, unidentified friend.

The reason the singer's 19-month romance with the Boardwalk Empire actor ended, according to a source, was because of their bicoastal lifestyles. "There was no bad blood and no third party involved," the source told Us. "It was honestly just a long distance relationship and it became too hard to make it work."

Ashlee's older sister, meanwhile, is quietly gearing up for the arrival of her second child with Eric Johnson. (The betrothed couple welcomed daughter Maxwell May 1.)

"It definitely wasn't planned," a source told Us of Jessica's bun in the oven. "But yes, Jessica is pregnant again."