I advise singles who date to examine the prospects with someone whom they date. When you go out, especially with a new person, find things to do that allow you to get to know each other, interact with each other, and that you both enjoy. Some examples, along this line, that people report to work well include bowling, miniature golf, a museum or botanical garden. Such activities are fun, they feel light and comfortable, you communicate (if you can't find what to say by yourself, you can talk about what you are seeing or doing to "break the ice"). Do not go to a movie, a show or anything that precludes interacting with each other while you are doing it. It is a mathematics axiom that parallel lines never meet. If you and your date are parallel lines watching a stage or screen, you don't meet! Besides, there are serious halachic problems with the content of most movies or shows these days, so they are generally not suitable in Jewish law. Choose activities that allow you to interact. Enjoy your time together and spend a sufficient amount of time to get to know each other REASONABLY well (note: before marriage, you can't know any person PERFECTLY).

When couples are getting to know each other more, after a few initial dates, I recommend that they go out for a full length day-trip (e.g. drive out-of-town to the country - making sure to keep the laws prohibiting Yichud/seclusion), perhaps doing this more than once. By spending a prolonged period of time, people tend to become more and more themselves as a day stretches out. You more and more get to see the real person in greater depth. You get to see some of the foibles or inconsistencies and some of the ways the person interacts with relating partners or challenging life situations. As you get further into your day, more of the real person comes out. There is only so much that a person can act. Over time, the guard goes down more and more. You may, for example, see if the person is ever critical, mean, inconsiderate, impatient, selfish or dishonest. Even if the person is nice to you, is the person's conduct rude or condescending to a waiter or gas station attendant? Does the person get angry, nasty or vulgar in a traffic jam? Does the person speak loshon hora [slander]? You can better judge - and have more insight into - whether this is someone you can really relate to, trust and appreciate; whether the person's good qualities are sincere, stable, consistent and authentic. There is no guarantee that a person won't maintain an act. I've seen some really shrewd, troubled, insecure, manipulative people who consciously hide their faults well until a relationship is quite developed and another person is emotionally "hooked" or until after marriage. However, there can often be signs, if you know how to read them. For example, Chazal say that you can tell who a person is by who he praises. Does the person praise Pirkei Avos or Dow Jones, the Chofetz Chayim or the Super Bowl, doing chesed or a shopping spree?

I am not suggesting that you ever "trap" a person. I am just saying to enter into situations in which the person is more likely to be his/her honest self, and behave his/her own way. Observe and learn from "real life situations" about how the person handles provocation and whether the person has any temper or character weakness. Do not intentionally provoke the person yourself. That would be a sin and no shidduch can be blessed if it comes about through any sin, whether deceiving, instigating or any other sort.

If a person has very good midos, a strong striving for truth and to generally behave as a "mentsh" [decent, mature, honorable human being], has considerable and authentic will to work on him/herself and the ability to do tshuva [lasting and reliable repentance] for wrong conduct; and if the person can relate and communicate in a genuine "two-way-street" fashion; the person who had a rough history might be able to fulfill the role of spouse and parent satisfactorily. Do not make a decision about such a person or relationship alone nor hastily. Investigate thoroughly so you "go in with your eyes open," and obtain da'as Torah and the advice of wise, mature, objective and concerned people. The more that you have suspicion, the more you should obtain information and verification of that information.

Have at least one, preferably several, QUALIFIED and caring advisors (e.g. rebitzen, rabbi, counselor) who know you reasonably well. One may catch something another missed, or have input the other did not have. Get OBJECTIVE input. Talk over impressions, events, reactions, behaviors (of the person you are dating and your own) and whether your various feelings are helpful and reliable or not. Don't be too hasty to either accept or reject a prospect for marriage. You don't want to get hurt, whether for marrying OR dumping someone you should not have. You must have BALANCE (as with all things in the Torah).

In any of these cases, all we can really do is increase chances for the good, not guarantee anything. The point for everybody is: 1. well-done Hishtadlus (practical effort); 2. each single truly being the best and most marriageable person (s)he can be; 3. and prayer to Hashem for mercy, help, success and blessing.