I have been going out with a young lady, and we are close to getting engaged. She is everything I am looking for, and we talk easily and enjoy each other’s company. Something came up on our last date, however, that is disturbing and makes me question where to go from here.

The girl said, “I think I should tell you that I have debt.” It seems that she borrowed a large amount of money for graduate school. She started school, using the money for both tuition and living expenses, which is allowed by the terms of the loan. Then she dropped out during the first semester and found a job. Her family somehow spent the rest of the loan. Basically, the money is gone. Her family is not able to pay it back, and the loan is on the girl’s name, so she is responsible for it. That means that, if we get married, it will be my responsibility as well.

To the Shadchan:

I’m in yeshiva, recently started in shidduchim, and I have had a few disappointing experiences. A couple of times, when I picked up the girl at her home and saw her for the first time, I immediately knew she was not for me. I was certainly gracious and tried to find common ground with her on the date. Once, I even gave it another chance with a second date. But in my heart, I realized that my first reaction was correct and I would not be able to continue. This happened after a long process of checking her out, taking off time from yeshiva, possible travel, and expenses, such as renting a car.

To the Shadchan:

I’m a regular Baltimore girl. I live at home with my parents and work as a professional. I’m considered pretty and accomplished, and have everything going for me. At 25, I’ve been dating for five years and am finding at least one aspect of it very stressful.

I keep hearing from shadchanim, my mother, and people in general that I should be going to shul and to other events and gatherings so that people will “see you and remember that you need a shidduch.” I’m constantly told that I have to look my best at all times – including makeup and perfect hair – whenever I leave the house.

I am a 23-year-old man. I work and also go to college, and I am getting ready for my first date. Of course, I am getting lots of advice from friends, brothers, and my Mom. Unfortunately, much of it is conflicting advice. For instance, I usually wear casual clothing. Do I have to wear a Shabbos suit on the date? Will the girl be insulted if I don’t? I would also like to know how long the date should be. I have heard everything from going out for coffee to a three- to four-hour marathon. What do we talk about for all that time? How personal should I get? People say, “Talk about your family.” Well, how deep do you go with a perfect stranger? How much does my date really want to hear? Do I open the car door before the date? Afterwards? Do I just drop her off or walk her to the door? I haven’t seen any men do these things once they’re married, so isn’t it a little artificial? Finally, a friend of mine’s wife set us up, so am I expected to go through her for a second date, or can I just ask the girl out again if I want to?

To the Shadchan:

My neighbor’s oldest daughter has just started going out, and I have a gotten two calls, so far, about her and her family. People know that I am her neighbor, so they call me. I am in a quandary, because I know too much. My neighbor is a very nice and warm woman, but she suffers from terrible shalom bayis problems as well children with health problems and learning disabilities. I am her friend and sounding board, so I don’t know what to say to callers. I don’t want to hurt my friend or her daughter, who is a nice girl and deserves a chance. But I also don’t want to mislead people. If they ask specifically about these issues and I am evasive or don’t answer, I know that people will assume the worst. Even if the caller does not ask about shalom bayis, am I supposed to volunteer the information? Would I be guilty if not telling this information were to cause problems down the road? What is my responsibility? What is a smart way to handle it?

To the Shadchan:

My older daughter got married a few years ago. The whole shidduch process went very smoothly for all of us. She was a typical kind of girl. She went to a typical seminary in Israel, came back, and started to work and go out. She had lots of friends like herself, and she wanted a typical type of boy.

My second daughter now wants to start dating. She is more of a loner, who does not have a lot of friends. There is something a little atypical about her. For instance, she doesn’t seem to be aware of fashion. (She likes to wear hats in the winter, which makes her “different,” silly as that may sound.) She also tends to be moody and emotional.