Jake Gyllenhaal steps out with Rashida Jones on Sunday, Anna Kendrick on Monday

Jake Gyllenhaal was quite the ladies man this Labor Day weekend, as he scheduled two dates with both Hollywood starlets, Rashida Jones and Anna Kendrick.

While it’s unclear if Gyllenhaal was romantically stepping out with both ladies or if one, or both, of the dates were strictly platonic, he started off his string of dates with Parks and Recreation star, Jones.

E! Online reports that the two, along with Gyllenhaal’s dog Atticus and three friends, lunched at Los Angeles' Café Gratitude on Sunday. The pair even left together.

On Monday, however, Gyllenhaal flew to Las Vegas to meet up with his End of Watch co-star, Kendrick. USA Today reports that Gyllenhaal had his arm around Kendrick on the way back from lunch, after spending the holiday with a few friends in Sin City.