Can You Suggest Shadchan Learning Resources? Shadchans willing to mentor?

Dear YWN,

I’d like to create a better Jewish dating site, and as part of my research, I’m trying to set up friends. (Lest you think it’s hopeless – Thank G’, some friends my wife and I set up got married last year. :))

My questions:

1- Anyways, I’m curious if you guys know any good learning resources about it? Books, blogs etc?

2- A related point is that I’d love to get some mentoring/apprenticeship type thing with a shadchan. (I live in Jerusalem, if you have any local recommendations that’s awesome. Otherwise, happy to learn via skype etc.) Recommendations welcome, please :).

3 – I was wondering what would happen if a friend who I thought was unattractive came to me? How do I respond? For example, what if it’s a guy who smokes or is [very] socially awkward? What about a girl who’s really heavy (not just curvy, but really overweight)? I feel a bit hypocritical because it’s not so hard [mentally] for me to set up someone who has a problem with middot even though I recognize it’s equally as important.

The reason smoking/social awkwardness/heavyness is harder to deal with is because you can’t omit saying that, since %-wise many more people care. Whereas if a guy talks lashon hara or a girl is dishonest (but otherwise they’re attractive physically/personality), some people will overlook that/not realize it’s an issue/find excuses. You want to help people dealing with these challenges, but how do you tell potential dates? Just show a pic? Decline to set them up in the first place?

I don’t think it’s fair to decline – especially since I’ve personally seen women who were moderately chunky up to really heavy (partly genetics in that case), get married. But I don’t know how you might manage expectations. Say something like, “I will do my best to find you someone, and b’H He will send you the right person. I think you’re fantastic and will emphasize [insert genuine point of admiration] to potential dates. That said, I don’t want to get your hopes too high. Unfortunately, it’s a known thing in the dating scene that a fair number of people won’t go on dates with someone with [your problem x ].” ?? I feel like that last bit presenting the problem isn’t smooth enough…

4) I’m trying to interview north american single Jews (especially in their 30s) to find out what they find most challenging about finding the right person. Being 25 myself (I’m married, if you’re wondering), I don’t know that many 30+ people, and asking for references often gets a refusal because people are afraid to insult friends (they don’t want the single friends to feel pitied/looked down upon for being single). Any thoughts, advice or willing volunteers in this regard would be great.

(What I’ve done: spoken to as many friends in my Facebook contacts as possible, some people have been great and referred their friends, I tried Amazon Mechanical Turk since it’s apparently represenatative of the US pop, and maybe a couple other things.)