Dating has been under represented in computer games thus far, which is a bit strange given its interactive nature. However, as most games are aimed at teenage boys, although they might like the sight of a page 3 girl, dating in its strictest sense is preobably not very high on the agenda.
One of the classics of the genre however is leisure suit larry. Following the exploits of the lounge lizard larry as he tries his charm with the ladies in his neighbourhood. Check out a clip here, it's hilarious!