Published on April 30, 2008 You must date a girl enough so that she likes you and when you take her home you will press "a" to try your luck and if your lucky you will get lucky and an achievement. For a quick way of getting this achievement follow what I did
After taking Michelle out on the initial date where you go bowling call her up at a decent hour to take her out again. For this second date I took her to the restaurant on the island you start off on (I think its the 69th street diner or something like that) After that date call her up the next day and take her out again (for this one I took her to the homebrew cafe to play pool, I also got the pool shark achievement while doing this.) when you drive her home press the "a" button to try your luck, and voila she should take you upstairs for some "hot coffee"