Jennifer and 29-year-old Harry - who is also the founder of Pink Taco restaurant chains - spent two-and-a-half hours having an intimate dinner at the exclusive Sunset Tower Hotel in Hollywood on Wednesday (01.09.10).
An onlooker said: "Jennifer was at a cosy corner table with a good looking younger man. She was twirling her hair a lot and flirting shamelessly.
"Jennifer looked really good. She had on white jeans and a sexy black tank top. When her mystery date left for the restroom, she took the opportunity to primp by reapplying her lipstick."
After the date, Jennifer - who was recently linked to ex-boyfriend John Mayer - slipped out the back door to avoid the waiting paparazzi.
Although Harry - who has also previously romanced 'Heroes' actress Hayden Panettiere - seemed quite smitten with Jennifer, he may be wary of dating another high-profile star as he has previously spoken of his dislike of having lots of publicity.
He said: "It is the worst thing of all time... I'll be happy if it never happens again. There are people out there who just love it. Not me."
