No matter if we’re 19, single, married for 50 years, or divorced... we have all asked ourselves the same question this reader has.
Dear Goldy,
I’m in my mid-twenties and have been dating for six years. I’ve dated nice guys, weird guys, wise guys, and old guys. I’ve never had a truly terrible date, but I’ve had some bad ones. I’m not worried that I’m in my mid-twenties and not married yet, even though a few of my friends are.
The issue: I’m dating someone I like a lot, but he’s not what I pictured myself marrying. Not that I wanted Prince Charming or a Rolls-Royce... but I expected someone with a little bit of yichus (meaning money). I don’t mean to sound snobby, but I was raised a certain way. My family lives a certain way. I have gone out with men from specific backgrounds—those working in family businesses or who have gone through medical school, law school, or some other white-collar profession.
My friend set me up with a friend of her husband’s. I wasn’t dating anyone and said I’d go out just to keep myself busy. But wouldn’t you know it; I ended up liking David* (not his real name). David isn’t like the other men I’ve met. He comes from a poor background; he’s not embarrassed by it, nor should he be. I’m mentioning it because it’s part of the issue—or should I say, my issue. David is a teacher. He works for the Department of Education. He teaches high school math, so he’s a smart guy, and he loves what he does. I just never pictured myself with a teacher. Nothing is wrong with being a teacher; I just never thought about it.
David will always have good healthcare, a pension, and steady work. One of his parents is a teacher and the other is a paralegal. He has a sister who is in college, undecided on a major, and a brother who is a computer programmer. All of this is fine. It’s just that I never pictured myself with such an... ordinary guy. I’m aware of how awful that sounds. I’m not a thesaurus; I’m not good with words. I’m not looking down on David - although it sounds like I am, but I’m not. I always pictured myself marrying someone who grew up like I did, from a family similar to mine—know what I mean? I don’t consider him poor or from “the wrong side of the tracks” or anything like that. The truth is, I just never pictured myself marrying a teacher.
I spoke with my parents, who told me the choice is mine and they will support me if I choose to see where this relationship can go. My parents aren’t snobs, and they don’t act as if they’re above it all. They fully support me if I choose to marry David, if things go that far. But I made the mistake of mentioning this to my friend—not the one who set me up. My friend didn’t laugh, but she wasn’t very supportive either. She said if I like and can love David, that’s all good, but not to expect the same type of lifestyle I always thought I would have. In this relationship, I make more money. I may not be able to be a stay-at-home mommy when the time comes—or who knows, that’s years away.
I am the one with these issues, not David. He hasn’t spoken about money or lifestyle, but then again, we’ve been dating for only a month. When is the right time to bring up the subject? You’ve written about that, too. This letter sounds like I’m looking down on him or his family. I’m not. I just don’t know what to think because I never pictured it like this.
— Shira
Thank you for your letter, Shira.
I don’t think you’re a snob or looking down at David, his job, or his family. Simply put—this is just not someone you ever imagined marrying (for whatever the reason). But now that you’ve developed feelings for David, you’re confused about what to do.
Life isn’t always how we imagine it to be when we’re children. Nothing is wrong with thinking about your future and imagining how everything will be, but this is where you are now. What will you do?
Your first “problem” was saying yes to a date that you were never really interested in or invested in from the start. You wrote that you had nothing else going on, so you said yes. Well, now look what happened! Make decisions with the thought: This decision can change my life; how would I feel about that?
I’m not saying to let go of your dream—whatever that is. But look at what is real and in front of you. David is a great man whom you seem to really like. He doesn’t check all of the boxes, but are those boxes deal-breakers? He’s not a doctor or lawyer, and he may not drive a fancy car—but is he a good person? Does he make you feel good about yourself? Does he have all the maylos you’re looking for in a spouse other than the exterior? Can you see him being good to you (and your family) for the next 20 or 30 years?
You wrote he has a good job as a teacher. Unless the NYC Dept. of Ed. goes bankrupt or schools are abolished, David will always be employed and have good benefits. I grew up in a “Board of Ed” house (it was the Board of Ed in the ‘80s and ‘90s). Both my parents worked for the Board of Ed; they always had good health insurance—they still do—as well as a pension. There’s nothing to be embarrassed about there. He is working at a job doing something that he loves. You have to be pretty smart to be a high school math teacher, and pretty tough, too, if he works in a public school.
You wrote that your parents don’t care about all these little things jumping around in your head. I’m sure they don’t. I don’t care how much money they have—if they are good parents with sechel, they will trust that their daughter has made the right decision for herself. They will welcome David into the family with open arms, just as they would a doctor or lawyer. To them, it doesn’t matter; your happiness matters. Your friend, on the other hand, knew exactly what to say to make you overthink this.
An important question to ask yourself is: Do you respect David? If the answer is yes, great. If you can’t respect him because of his profession or for any other reason, the relationship will not work. Respect is a must in every relationship. Now, if my mother (zt”l) were here, she’d ask, “Can you see yourself washing his underwear?” That too would lead you to the answer of whether you could see yourself with David ten years down the road.
You can’t always line up your ducks in a row. This is life, and life throws curveballs. You weren’t expecting to like a “teacher,” but you do. Now it’s time to grow up mentally. You may be in your mid-twenties, but you need to think like an adult. Does not having a pristine white-collar job matter? Does the fact that you will earn a larger salary bother you (or him—and yes, have that conversation)? It may mean that you have a three-bedroom house instead of a four- or five-bedroom house, or that you may have to work and not be a stay-at-home mom. See the cup as half full, not half empty. It’s all up to you and how you choose to see things.
Having the yichus you spoke of often means nothing. Someone can come from a wealthy family and have no manners, acting like a spoiled child. I went out with such a man-child once. His family was very wealthy, but his behavior was erratic and he said rude things... but he had the money behind his name to back it up—or to give him the confidence to act like a jerk. He knew he had his pick of “girls” to date, so he didn’t care how he acted. But let’s put him in a teaching job from a Board of Ed family like my own—would he act the same?
A jerk is a jerk is a jerk. But if you don’t have anything to back you up or to “explain” why you act like you do, then no one will want to date or be around you. Money helps people act (or not act) like a mensch—it depends on the actual person, not the size of his wallet. The fact that David seems like a mensch without the yichus shows he was raised right.
I don’t think you’re looking down on David, his profession, or his family, but you may want to look up some new vocabulary words before you try to have this conversation with him or someone else—if you decide to.
My advice: Don’t overthink it too much. Just go with the flow and see what happens.
Hatzlachah to you all.
Goldy Krantz is an LMSW and a lifelong Queens resident, guest lecturer, and author of the shidduch dating book “The Best of My Worst” and children’s book “Where Has Zaidy Gone?” She can be contacted at This email address is being protected from spambots. You need JavaScript enabled to view it.. Goldy is an experienced dating coach offering private sessions. To inquire, contact her at This email address is being protected from spambots. You need JavaScript enabled to view it..
