On Wednesday evening, the Southpaw actor had a night on the town in Boston, where he headed to Cinquecento Roman Trattoria in the city's popular South End neighborhood. Along with seven male and female friends, Gyllenhaal was "catching up and relaxing" while the group enjoyed a bottle of Carpineto Chianti, an onlooker tells PEOPLE.
In addition to the wine, the group nibbled on salumi boards and ate the Tagliatella alla Bolognese, which features veal, beef, pork, pancetta, and parmagiano. Dressed casually in a white t-shirt and khaki pants, observers said the actor seemed to be in a great mood.
"He looked extremely happy and laughing with friends he hasn't seen in awhile," said a source at the restaurant. After the group departed, Gyllenhaal and friends hugged it out on the street and parted ways. Gyllenhaal has been spotted frequently in the South End neighborhood in the last couple weeks. Fellow shoppers saw him browsing the aisles at The Urban Grape, a wine, craft beer, and spirits store.
Jake Gyllenhaals Changing Looks
On Thursday, the actor headed to United Prosthetics in Boston's Dorchester neighborhood along with some of the crew of his film Stronger, in which he plays Jeff Bauman, who lost both of his legs in the Boston Marathon bombings. Gyllenhaal spent time with the group's prosthetist and Medical Director to learn about the bilateral above-knee amputations which Bauman underwent, and made sure to snap a few photos with staff.
Back in January, Gyllenhaal met with several of the bombing survivors to prepare for the movie, which is expected to begin filming in Boston this spring.