Do Orthodox Jews still use a matchmaker (Shadchan) in determining who marries whom? I have heard that matchmakers usually sort people of similar backgrounds for a match; while converts and Jews who are new to observance often get stuck with very little “high-quality” suggestions. Is there any truth in this?

Many people, even without realizing it, use a matchmaker of some sort. A matchmaker does not have to be a professional who is paid for his/her efforts. It can also refer to a friend who introduces two people, or even to an online service that matches bios. It is true that in the more Orthodox circles, young men and women do not usually find each other without someone checking them out first.

It is also true that converts and those who are new to Torah observance have a more restricted pool in which to find marriage partners. This is simply because Jewish parents want their grandchildren to have the benefit of two sets of grandparents from whom to receive their Jewish values, and with whom they can share religious observances and celebrations.

Additionally, there is a theory that partners of a similar backgrounds make the most successful marriages. Therefore, converts or newly observant Jews are often recommended for marriage to people of similar backgrounds.

By the way, unless specifically asked, a convert need not volunteer the information that s/he is a convert on the first few dates. This allows one partner to develop a sense of the other’s character without being prejudiced by his/her status. If the lady is the convert, she has to be careful about dating a man who is a Kohen (descended from Aaron), since a Kohen may not marry a convert.