To Friends:
How did you meet him?/ how long have you known him? When was your last contact with him?
Do you know the family too?
What is he looking for?
How would you describe his middos? (If they give an adjective, ask for an example)
How's his relationship with his family, friends, Rabbis?
Is there a specific Rabbi/mentor that he is close to? If he doesn't have one, who does he go to for guidance? Does he ask sheilos?
Is he the first or last to help clear the table / be at seder in the morning / be at minyan?
What does he do during his spare time?
Where do you think he would want to live long term, in-town or out-of-town?
What are his long term plans? What are his vocational goals?
How attached is he to his cell phone?
Does he have social media /watch /listen to non-Jewish music?
What is his relationship with his learning?
Why does he think it's important to learn?
How does he react when things don't go his way? How does he handle pressure? Have you ever seen him angry?
Did he face any challenges in her childhood? How did he deal with them?
What standard of living is he used to? What standard of living will he maintain after marriage?
How does he dress during the week? How does he dress for Shul/on Shabbos?
Is he overweight or overly concerned with his weight?
How tall is he?
Does he smoke? Does he have any signs of addiction or obsessions?
Does he have any medical or emotional issues that I need to know about? If yes, how long ago? What was the treatment? How has he recovered?
Can I call back if I have any other questions?
To Family References:
How do you know the family and for how long?
Do the parents get along with each other? (You can ask this even if they are divorced)
What are the parent's relationship with their children?
Do they often have guests for Shabbos?
Are they active in the community and give an example?
Does he have neighborhood friends?
What is the relationship with the son/daughter-in-law(s)?
What do his parents do? What are their hashkafos and their cultural background?
Stories about the family that bring out any other points?
Are there any mental/emotional issues with the family?
To Rabbi/Mentor Reference:
How have you seen him grow? Is he actively striving for growth?
Is he the first or last to minyan or seder?
Does he have social media / watch / listen to non-Jewish music?
What are his plans for the near future and long term?
What is his relationship with his parents and siblings?
Does he have friends? Is he the type that he's friends with everyone or does he stick to his chevra?
Does he take learning seriously or does he schmooze?
Dor Yeshorim:
It's generally accepted to check Dor Yeshorim compatibility prior to the first date, or after 1 or 2 dates (before it gets serious).
Ask the shadchan to get the boy's 9 digit Dor Yeshorim number and his date of birth.
Either call Dor Yeshorim’s 24 hour hotline at 718-384-6060 or go to doryeshorim.org/check-compatibility/ and enter both side's information. They will give a call back with the results.
Additional Resource:
Binyan Shidduch Center has a list of research questions here.