Orange beauty Jessica Simpson looks a bit gloomy. She looks gloomy while exit the Beverly Hills Hotel in Beverly Hills, California. Jessica Simpson is 28 year old. She is country singer’s boyfriend, Dallas Cowboys quarterback Tony Romo, recently mentioned his dream date with Jess, saying,- A little bite to eat and probably watch a football game! She loves the game. It’s exciting for both of us. I’ve found someone that I get to hang out with and who wants to see our team do well!