Things I remember from dating:
1) If someone is not ready to date or resistant to dating via shidduchim do not push them. There is nothing more frustrating to that person or to the poor individual they end up on a date with.
2)What someone's parents want may not be what the single wants. Make sure to get the singles perspective as well.
3)Ask about how outside the box the person is willing to go in terms of age, background etc. Sometimes the answer will surprise you.
4)Follow up! No one wants to have to call you about the shidduch you mentioned but never pursued. It makes them feel desperate, no matter how nice and scatter brained you are. Even if it is a no, let the other party know so they are not wondering.
5)Make sure there is communication after the first and second date. If the couple has taken things into their own hands, fine. But if no one has addressed the issue of a second date then you should. Even if it is just to clarify that there will not be one. Try to stay involved until at least the third date. Everyone will have more peace of mind.
6)Sometimes the best thing a shadchan can do is help sheperd the parents through the process. The couple may know it's a yes but the parents start freaking out the minute they meet the in-laws, plan the vort, realize they are loosing their baby etc.
7)It is best when you have had some sort of contact with the people you are setting up. Otherwise how can you really know them and their compatibility? Yet be mindful of the singles time. Getting dressed up for a five minute chat with some shadchan was every girls worst nightmare. (And I have never heard of a shadchan making a boy do this). Do not make them schlep in every two weeks to update you on their life.
8)If you are a professional shadchan working with someone and you have not had any prospects for them in a while, call them. Let them know you have not forgotten them.
9)Be discreet. Do not go blabbing about the couple you set up to everyone and their cousin, on the subway at the top of your lungs. These are peoples lives you are dealing with here.
10)Ask why a couple broke it off. Even if it is after one date. This helps you find someone more appropriate for them the next time. If they have no answer you may need to push a little. This is important as sometimes people feel it is lashon hora to tell the shadchan about a dates bad behaviour. But if someone is acting inapropriately you need to know! You don't want to be setting up numerous singles with the inappropriate person. Also, one person's inappropriate is another person's normal. So try and get some sort of idea what the problem is. If "inapropriate" was taking you to a bar on the first date there are many daters that are fine with that and you can adjust set-ups accordingly. If "inapropriate" was groping the other person you want to cease setting that person up. Assure the single that whatever is said remains between you two and keep that promise.
Some words for the daters:
1)I know that when your friends get engaged you hope they will set you up with some of their husbands friends. However, do not pester them during their engagement period. This is a very stressful time and it is not fair to ask them to jeopardize their relationship to try and get you a date. Many boys are not willing to set up their friends right away. Give it some time and wait until after the wedding.
2)Although good shadchanim try very hard to always follow up we sometimes forget I apologize for it but please call us. I know this makes you feel desperate and horrible but we really did just forget and are glad of a reminder.
3)Get out there and meet us! We can't set you up if we never met you. Tactfully let people know you are open to being set up. I myself never try and set people up unless they are open to it. Often, we will ask you when we meet you. However, if you know someone is a matchmaker there is nothing wrong with slipping into the conversation that you are available and that you appreciate any suggestions they may have for you. Just do it tactfully, not in the middle of a room full of people who are listening to you.
4)Be honest with us about what you want. Otherwise we are not going to get anywhere.
Good Luck to all the daters! May you all find your match soon.