Tons. You'll be asked many times, but they are mostly all the same. That is, the dates go the same way, though they have different preferences for your look and attire. You can go on dates to different locations and it sometimes unlocks a specific sex scene (like a scene at a movie theater). If you go on many dates and your relationship improves, your boyfriend/girlfriend may ask you to change your appearace, sometimes drastically, so be aware of that, because sometimes you may not have a choice (I'm not sure if this is related to submissiveness stat that you will agree without there being a choice or if it is just based on how strong your relationship is). You can have multiple boyfirends/girlfriends at once. Finally, note that after a while I found them mostly a pain and they constantly call and interrupt your day , but you should definitely try dating both sexes for a while if you want to see the variety of scenes that have been created. You can easily break up with them at any time, and another one will be hitting on you in no time if you are pretty.
