Throughout my dating career, I've dealt with many different types of shadchanim, be them amateurs just getting their feet wet, friends or family members that had a shidduch idea and were acting as a go-between, or career shadchanim that are at any time working multiple matches.
There are a few basic rules that I feel anybody setting a couple up should abide by. First and foremost, you must be reachable! Once you set a shidduch in motion, you cannot drop the ball. I've been in situations where a shadchan didn't get back to me until two weeks after a date. I'd reached out to her multiple times in those two weeks, and she just didn't respond. Granted, in that scenario, I had called her immediately following the date and expressed my horror regarding how the guy had acted. She apparently didn't feel like she needed to follow up after having spoken to him, because there would be no second date. However, I needed the closure -- just a short phone call, text, or email letting me know what happened (and as I eventually found out, there was a "his side to the story," but it was too little too late).
In a similar situation, a friend's husband had set me up with a friend of his while I was in their city for the day. We had a fairly good meeting. It was supposed to be an hour --tops-- coffee date, and we ended up stretching it to a little over two. We had gone into the date saying that we would meet, and if we both thought it had potential, we would exchange resumes/profiles and take it from there. Following the date, we both said we had enjoyed each others' company and we were interested in proceeding. To me this meant that we would continue dating and we could "do research" about the other person while we did this. I waited for about a week before my friend's husband got back to me (I had to chase him down). He said, "Someone else in his city came up in the mean time, so I guess that means he doesn't want to pursue this right now." You really made me wait a week to tell me he's not interested? To this day I'm not sure if my friend's husband made up that response to try to "soften the blow" that he didn't want to date me, or what. Just be upfront, be honest, and please be timely! I could have been pursuing something/someone else that whole week.
The best case scenario is when the shadchan touches base with the girl within a few hours following the date, or the next morning. It's protocol for the shadchan to talk to the guy first. If he doesn't get in touch, then as the shadchan, reach out to him and find out what he thought and if he wants to go out again. Then, call the girl.
Especially if the couple hasn't exchanged phone numbers, it's important for the shadchan to be accessible in the scenario the guy or girl is going to be late, gets lost, or can't seem to find the location where they're meeting.
A good shadchan is on top of times, locations, and other logistical details. I've been in situations where, for whatever reason, the shadchan told one of us the wrong time, and either the guy came to pick me up fifteen minutes early (poor parents, they had to entertain him, because I was not ready), or he was waiting for me in a hotel lobby for a half hour, because the shadchan never updated me on a time change.
It is possible for a go-between to "ruin" a shidduch. I can't remember exactly what went down in this particular case, but I do know that there was a situation in which there was a misunderstanding regarding who was traveling for the date. In the end, I think I just gave in and went to him (even though I think I had traveled for the last two dates as well), but not without some resentment. The whole situation could have been avoided had there been better communication and the shadchan not assumed anything, nor told either one of us what the other had "said," as neither of us had said any such thing. This wasn't the reason we ultimately broke up, but it sure colored it for both of us.
Another aspect of open communication is, despite how uncomfortable it may be, to extend the courtesy of letting someone know if your suggestion declined interest in going out altogether. Meaning, if you mention an idea to someone, letting him know that you're redting the suggestion, and consequently the other party says s/he isn't interested, it's a nice practice to let the other person know this so he isn't wondering what's going on.
On a different note, I understand why a shadchan would "push" a shidduch, because admittedly, sometimes singles have stupid hangups and they need to be encouraged. Encouraged, not coerced! A good shadchan will help a single explore what's holding her back or turning her off. Sometimes one (more) date isn't a bad idea, but sometimes it is! There's enough internal pressure and desperation as it is, so please don't try to force anything.
Feedback is also crucial in a shidduch. There's one shadchan that I've worked with multiple times, and he always asks for feedback following a date. Sometimes it's annoying, because I don't always have feedback to share after a first or second date, or I don't really want to outline why I don't think the guy is for me, but it's helpful in other situations, especially when he shares the feedback from the guy.
As an aside, that's one of the positives in shidduch dating. Despite it making the relationship a little more superficial, there's a way to know what the other person is thinking/feeling about the relationship before you feel familiar enough to have that conversation with the person himself. It can be helpful in multiple ways.
Being a shadchan is sometimes a thankless job, especially when you spend a lot of time trying to convince people to go out and they don't want to/never "say yes" to your ideas. Sometimes you don't know what's right and how to proceed. I obviously don't have answers for that, but I do think that some of the things mentioned in this post can help pave the way for those shidduchim that do make it to first base, er, I mean first date.
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