Before someone is born a bas kol goes who out saying who his zivug is. That bas kol comes 40 days before you're born. Don't expect to hear it on the date. That means there are no fire works, bells, pink fluffy clouds, music playing, or anything of that sort indicating that she/he is your bashert.
Sometimes bringing a game on a date works very well. I brought games on dates many times, but I didn't use them every time. Some good games are: Scattegories , Taboo, Balderdash... I found that games that involve talking and thinking often help spark conversation, and some games can be good tools to open conversation on a deeper level.
My Rebbi told me when I started dating that first dates are like an interview to see if you want to go on a real first date. I think that he meant first dates don't count that much and unless you are sure the potential shidduch is not for you, go out again. (This doesn't mean act like you are at an interview though.)
Don't have a predetermined idea that the specific date you are up to means that you need to feel a certain way. All people are different and all situations are different. One of my friends went on five dates with a girl and felt as if he was still on a first date with her. They continued dating, and are now happily married. I have another friend who got engaged on a fifth date. Each individual has to gauge himself on his own personal scale and not start jumping to conclusions based on the numeric position of his dating.
The classification of a date as a "fun date" is a little misleading. While a fun date may and can be fun, don't expect it to be like going to an amusement park with a bunch of your friends. Dates work with a completely different dynamic than regular every day life and this changes the whole situation. Just keep this in mind when going on a "fun date." (For example, you may have had one or two good dates and then go to New Roc City and not have a great time. That doesn't necessarily mean you should stop dating that person, it means that you should give it another shot in a different setting.)
Calling the Girl
Calling the girl before each date may seem scary but it is some of the most practical advice I ever heard. Even a two minute phone call before a date is a huge icebreaker. Also a lot of the aggravation of the phone tag aspect of shidduch dating is eliminated. The phone calls grow longer as the relationship grows and it helps to increase your comfort level. Some people disagree with me on this point, you can speak to them if you meet them to discuss it.
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YOur 2 Cents: When in doubt
One of the more practical bits of advice that I was given is that for the first two dates or so, you should say yes to another date unless you have a reason to say no. After that you should have more of reason to continue your relationship.