To the Shadchan:

I’ve gone out with a girl several times, and I really like her. She is very empathetic, kind, and loving, among other wonderful attributes. Although we met casually, and not through a shadchan, we seem to have the same religious hashkafos. We are both graduates of similar day schools, but our homes are somewhat different. I come from an upper-middle class background – the kind of home that is described as “balabatish,” with all the positives and negatives that that term connotes. Her family is more freewheeling. For instance, her siblings are all shomer Shabbos but of various types.

On our last date, we got on the topic of children, and she said she would not want to send her children to one of the long-established day schools, which we both attended. I already knew we were not on the same page politically. I am a lawyer and a political conservative. And I see that she mostly agrees with what I consider extreme liberal views. She looks at things from a very personal point of view – like how people feel. While I admire her good middos and compassion, I don’t think important policy decisions should be made on the basis of emotion.

I am a mother of a daughter in her mid-twenties. During her teenage years, she had a rough time. She was involved with drugs, dropped out of school, and got into a lot of trouble. She has matured and is now a law-abiding citizen. My problem is that it is very hard for me to advocate for her in finding a husband. Aside from her history, I see her faults clearly, and I am not sure if she has the attributes necessary to be a good wife. She does not have skills to earn a good living, although she is working towards her AA degree. She argues a lot with her siblings, is not helpful in the upkeep of the house, and does not have good social skills. The truth is that, if I had a son, I would not want him to marry a girl like my daughter.

Still, I care about her and would love to see her married and settled. I just don’t know how to approach the whole subject. If I tell shadchanim and my network of friends the truth, they will not look for a shidduch for her, but if I don’t tell them the truth, how can I live with myself?

To the Shadchan:

I have been dating for seven years now, and this is my story: I am a professional, pretty, and have a good personality – at least according to my friends.

At this point, most of my friends are married and busy with small children. Besides, they no longer seem to know eligible guys. They know lots of shadchanim, though, and every time a new one comes to town, I get a call: “Did you know that Sara the matchmaker is coming? Oh, you’ve got to call her!”

I’ve met lots of shadchanim. There was a time when I would drive to New York and Lakewood to meet them. I decided that it was a waste of time as they have girls in their cities to set up. Let me tell you, going to a shadchan can be overwhelming. Some of them think they can ask you the most personal questions. It is demeaning! It is almost if you are going for a job interview, except I don’t think a boss would dare ask the questions I get asked – like, why aren’t you married yet? And what are your three most prominent attributes? They seem to just go down a standard worksheet. And in the end, do they ever have an idea? No! Nothing. Some shadchanim actually engaged me in conversation and seemed interested in me as a person, although they, too, did not have suggestions. But at least it was a positive experience.

To the Shadchan:

My daughter got engaged. She is very happy, and we are happy with the young man. The problem is that our family is more modern than that of her fiancé. Now that we are planning the wedding with his parents, I find that we are not on the same page about anything. The first point of contention is the date. I feel I need a year to prepare properly. The other side wants it as soon as three months from now. They also want everything very scaled down. This is our first child to get married, and we want a beautiful affair. The only simchas we have made were bar and bat mitzvas, which were very elegant. I know I can be a little over the top, but that’s who we are, and so are our neighbors and relatives. That’s what people expect in our circles.

I’m okay with paying more to bring my vision to life. But his family seems to be philosophically opposed to what they call a “fancy” wedding. We are fighting about everything: the date, the kind of hall, the invitations (and whether to ask people to “dress in accordance with Orthodox tradition”), the style of music and dancing, and the height of the mechitza.

Dear Rebbetzin Katz, 

I realize that your goal is more than just getting a couple under the chupa but also making certain that the simcha between the chassan and kalla is a lasting one. My husband and I find ourselves dealing with some issues regarding my son and his kalla that give us reason to worry about that outcome.

Some background: Our kids have all chosen different paths along the “derech” – some to the right, some to the left – and their spouses reflect those choices. As a result, their desires and needs before and after their weddings have varied widely. We tried to be even-handed with our children, setting aside money over the years to help them achieve their goals: getting through yeshiva, undergraduate, and sometimes post-graduate educations. We have made weddings and helped them get a start in their married lives. The amounts for each child were roughly equivalent, but the way it was spent has been different. For instance, one kalla is a baalas teshuva who wasn’t into jewelry, and she chose other things instead of the usual kalla gifts. We paid for another son who chose to go to graduate school and have a very minimalist wedding, while his more yeshivish brother, who is now the chassan, went to Eretz Yisrael to learn post-high school (which wasn’t for free).

To the Shadchan:

Recently, we got a yes from a boy, so we started looking into it. Three days later, we told the shadchan that we were interested but were told that the boy was busy at the moment. That was frustrating, but we moved on. A couple weeks later we got another yes. This time, we did our research in two days, because we didn’t want a repeat of last time. We said yes and were then told by the shadchan that the boy was very busy at work but will be in touch. Two weeks later, I hadn’t heard anything, so I reached out to the shadchan again. We were told that he was very interested but was still busy with work. Also, he is from New York, so there was not so much travel involved, and I was willing to meet halfway. It has now been almost four weeks, and we haven’t heard anything from him. We are very frustrated. Any advice?