Jake Gyllenhaal was definitely not winning when he asked out Derek Jeter's girlfriend Minka Kelly, although she was really Derek Jeter's ex-girlfriend at the time. According to a report in US Weekly, Jake asked Minka out in the fall and she declined. See that is such a polite way of saying no. It would be funny if she said, "I decline." I have given up asking anyone out because you get tired of hearing no. I think I might hold the world record for hearing the most "no's" in a foreign language. Honestly, considering that half of the women on that list had been speaking English to their friend a minute earlier, I am pretty sure whatever language they were speaking was probably made up. You have to give Jake credit for trying, although I am sure he is way more used to hearing yes than no and kind of takes it for granted at this point.