Guys should ALWAYS walk the girl to her door. It is simple good manners and a safety issue as well, for many young women. Bowling is fun, can be a real ice-breaker (especially the horrid way I bowl, which was always good for a few laughs), but I think in general,with few exceptions, a pool hall is not the best place for a frum couple to go. Many of them are known hangouts where a great deal of drinking is going on, as well as inappropriate language and smoking. there are better places to go.
The issue of sharing food is a dicey one, since it is considered so intimate an action, that it is a hilchos niddah issue. I do think that if a specific dish is ordered at dinner, such as a pupu platter or chummus platter, dishes which are designed to be shared, that it could be less problematic for one who is concerned about it.
As to complimenting on a date – well, there are compliments, and then there are COMPLIMENTS. Telling a date he or she “looks nice,” is not the same thing as saying, “WOW! You look HOT!” The former is a simple and thoughtful thing to say, the latter, however, is best said (if that expression is used at all) to one’s spouse, if one is so inclined, when not during a niddah time. I do get annoyed when I hear that a girl got all angry at her date for having told her she looks nice. Someone posted something liek that in The Jewish Press some time ago, and I thought the girl got all bent out of shape over nothing. She should have been appreciative of the fact that the guy realized the effort she had made to look attractive on the date. the only proper response, is a simple THANK YOU!
If the date is going really badly, I don’t think there is anything wrong with pleasing a headache, not in a nasty way, though, and asking to go home a little early. Still, if it just is a matter that it is not clicking, I think everyone should give a date a real chance. In my opinion, however, it is wrong to get a guy to spend a lot of money first and THEN decide to have a headache. My daughter has been on several dates with different fellows who were not for her for wahtever reason. She nonetheless was an interested and interesting conversationalist, a polite and friendly person, and no guy could ever say he had a bad date when he was with her, even if it was not the right shidduch for either of them.