To the Shadchan:

I am looking for some direction. I am a 39-year-old single woman working in an office. I’m happy with my job, and I have good friends that I like to spend time with and travel with. I live with my parents. I could live on my own, but I enjoy my family’s company. We are very family-oriented and often get together with extended family, including my siblings and many nieces and nephews.

Recently, someone suggested a 40-year-old guy from Florida for me. As always, my mother started calling around to find out the basics, and when the prospect sounded interesting, she made a barrage of phone calls to his references to find out more details. The guy had said yes, but when he was told that my mother was making all these calls, he was turned off and changed his mind.

To the Shadchan:

I am a yeshiva bachur, aged 24. I have been going out for a year and a half. All the shidduchim have resulted in just two or three dates before the girl or I called it off. Now I have gone out with a very nice girl six times. The feedback I got after the last couple of dates is that she likes me but it’s not “going anywhere.” The shadchan told me that it’s time to start bringing the shidduch “to the next level.” By that, she means that I am supposed to have some “deeper discussions” and “open up” more. She didn’t give me much more guidance than that. I’m not a very emotional person, and I’m not quite sure how to go about it. What topics do you suggest that will help us form a better understanding of each other’s personalities, perspectives, and goals? Is it all a matter of abstract discussion, or is there some other way to connect on a deeper level? All this seems kind of artificial to me, but I’ll give it my best shot if it will help.

To the Shadchan:

Our daughter came back from seminary very idealistic and in love with Eretz Yisrael. Her dream is to live in Israel forever. In the almost two years since she’s been home, she has been studying for an associate’s degree in a field that is practical in Israel. She is also working as much as possible and saving money for her eventual aliyah. I must say that she is very responsible – but she has not “settled down” or given up her dream as most of her friends have done. Whenever a suggestion for a shidduch comes our way, the first thing she wants to know is if he wants to live in Israel. If not, she refuses to go out with him.

My husband and I are worried that she is limiting her options to a very small group of candidates. I also wonder how realistic she is, since living in Israel requires a lot more money than she can earn in a few years or that we can help her with. But our main concern is that there seem to be very few young men who match her criteria. What should we do?

To the Shadchan:

I met a guy in graduate school, and we have been going out for a few months now. We have a wonderful relationship, and he is starting to bring up marriage. I think he would make a great husband. He is very nice, observant, and has a career ahead of him. And we enjoy each other’s company.

So what’s the problem? His mother. He is the youngest child in the family and is very close with his mother. In fact, at age 26, he still lives at home. I have met his mother a few times and have eaten there on Shabbos. She is a personable and intelligent woman but very overbearing and opinionated. For example, one Shabbos, her daughter and son-in-law’s family were also at the table. One of their children was misbehaving, and the mother was criticizing the way they handled it, right in front of the child. The parents of the child backed down. My impression is that she is used to everyone listening to her and doing what she says.

Also, she asks too many questions, about everything. She seems to know a lot about me – too much. She was widowed many years ago and doesn’t seem to have many friends. Her whole life has been about her children.

I grew up in a home where I was taught to be respectful to adults, and I would never say anything inappropriate. But I am worried. If I marry this man, it seems like it will be a marriage of three. I’ve seen marriages break apart over that scenario. I would be really sad to end this, yet I am afraid. Should I run while I can, or do you think this is a manageable situation? If so, how should I go about it?

A Shidduch Question:

I’m a 40-year-old professional woman who has not yet found my zivug. Although I am very well respected in my field, I unfortunately don’t get that respect in my own community because I am not married.

I am grateful that my family as well as friends and acquaintances are still thinking of me. But I don’t like the not-so-subtle pressure they apply when I turn down what I view as a totally unsuitable suggestion. They accuse me (in a nice way, of course) of being too picky, of not being realistic. They say I am being superficial and not giving people a chance. “Why not just go out for coffee?” they say. “What do you have to lose? Just give it a try. It’s just an hour of your time.”

I am getting flack from my family, too. They say I should just marry someone I enjoy spending time with and start a family already and not worry so much about what they call my “requirements.” What does it matter if he watches TV or not, or if he does or doesn’t go to shul three times a day. They don’t seem to understand that I have a life. With the preparation, the anticipation, and the disruption of my schedule, dating is exhausting. It’s not “just an hour.”

I am not inflexible, and it is not these specific issues that bother me necessarily, but some things are important to me. I’m not interested in spouse who watches TV for hours a day. I’m certainly not interested in someone who doesn’t have a job and doesn’t plan to get one. I work hard at who I am and at improving myself. I want a husband who does the same, someone I can relate to.

I do want to get married – but to an appropriate match. I know every guy in the Baltimore and Washington areas, and I know they’re not for me. At the end of the day, I’m the only one who knows what I can live with and what I can’t live with. Again, I truly appreciate the efforts of people who care about me, but I have to do what I think is best for myself. Am I wrong? How can I get that message across?

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.