Rabbi Moshiach Gadol Hador
We are experiencing a shidduch crisis. There are so many girls over the age of 20 who aren't married who are just wonderful in every way, and something needs to be done. The first thing we need to do is raise money to pay shadchanim to marry them off by whatever means they may employ. The Torah says that the only Torahdik way for people to get married is with a shadchan, and that is the way all frumme yidden have gotten married throughout Jewish history. Some people have questioned where this is written in the Torah, but they are obviously apikorsim who never learned anything and don't trust Da'as Torah.
We need to convince single people to just marry whoever they are set up with. After all, every suggested shidduch comes from shamayim and it's a mitzva to get married, so what more do you need? If singles just married whoever they were told to marry there would be no shidduch crisis. We just need more yiras shamayim here.
Of course, this does not apply to those of us who are blessed with wealth, good looks, and impressive yichus. Superior forms of life such as these should absolutely look down their nose at everyone else and NEVER accept a shidduch without making the other party suffer all manner of interrogation and begging to even hope for a shot. How far you go with this depends on how much lower they are in status than you are. Of course, if they are too much lower, just laugh them off. If they are close, make it clear who's the boss. If they are on a higher level, do what you need to do to get your foot in the door, then make them want you, then establish some kind of leverage -- but don't play around too much lest you lose the metziah. Consult Da'as Torah here, as always.
When it comes to the interrogations, you need to know what questions to ask. It is absolutely vital that you find out the financial status of the entire family. Nothing is more important. Otherwise how can you expect to know what you can demand? This is business, after all. If you have this month's best boy in Lakewood and you settle for only half an apartment, two years of support, and a size 6 you only have yourself to blame.
Next you need to find out what items and people the family is ashamed of. EVERY family has someone they are ashamed of, and every boy and girl has some kind of problem or flaw. If it is a serious one (like lack of money, lack of exceptional abilities, or an individualistic streak) you need to know this right away so you drop the idea. Finding out after the first date isn't enough, because you don't want to risk word getting out that you accepted a shidduch that's beneath you. Once you've lowered the bar, even inadvertently, you can never raise it back up. Be careful!
Even if the flaw is less serious (say, a great uncle was once caught glancing at a secular newspaper through a store window), you still need to know so you can use it as leverage to make the other party more openly desperate and wrangle more money and other perks from them.
On your end of the interrogation, say as little as possible and come across as happy and confident at all times. The other side is bound to show weakness before you do if you play your cards right.
My final and most important suggestion to solve the shidduch crisis is to come to me with all questions and do exactly as I instruct you. Why make decisions on your own when I can make them for you? Just do what I tell you and make sure to give me the credit and gratuity when it works out. If it doesn't work out, you need to daven harder and figure out what's wrong with you. Because, obviously, something is.
Hatzlacha!!!