DATING FORUM

Question

I get together with a group of friends on Thursday nights to chill, have cholent, etc. We got to talk about our dating experiences. We are all in our late 30s, never married, and we date girls in their 30s. We all have the same experiences in dating, so we know it’s not our fault. These girls want to be wined and dined. When we were younger, the girls were fine with going bowling, playing ping pong, going for pizza, ice cream, or for a walk. But as soon as the girls hit 30, they think they deserve a 4-course meal at a fancy restaurant. They expect it, and the guys who don’t wine and dine the girls don’t get another date with them. 

A few weeks ago, you wrote about men who are gold diggers. Wouldn’t you agree that it’s more common among women? Why should we professional men who work hard to make a living waste between $300-500 on a first or second date? But that’s what the girls want and they complain that there aren’t any good men out there. What’s even crazier is that the shadchanim agree with them and say that there are more good girls than good guys. Let these shadchanim spend thousands of dollars a year on dates and see them talk so big. What’s your take on this?

Response

I have long been a proponent that modern dating should take an example from the Chassidish style of the beshow and emulate their method of “dating” (sorry ladies!). In Chassidishe circles, regardless of how rich a young man is, everyone dates the same. A beshow is where the young man meets the young lady in a private setting of a home for a quiet conversation. The purpose is to quickly determine compatibility for marriage. The parents of the young lady are typically in a different room; nevertheless, such meetings are conducted and viewed as serious.

Contrary to dates in restaurants or other recreational places, one can never be certain whether the intentions of both parties are for having a good time or if they are truly marriage-minded. Regardless of hashkafic leanings, shidduch dating is not intended for entertainment purposes, yet sadly, that is how it has evolved. A young man’s appeal is often gauged by where he takes his date, how much time he invests in planning the date, and of course, how much he spends on the date. It has become a dollar and cents calculation rather than a determination of compatibility and shared interests and goals.

Your letter shows frustration and also pain, exhaustion, and a tinge of disillusionment. And while I understand why you and your friends feel resentful, I also think the conversation needs to be reframed, because the issue is far more complicated than young ladies want to be “wined-and dined.” While there are young ladies such as what you describe, not every case is about greed. This also happens to young ladies who carry years of disappointment, insecurity, fear, and emotional fatigue.

When people are younger, dating feels lighter. A girl in her early 20s can happily go bowling or split an order of fries at a pizza shop because she still feels hopeful. She believes marriage is around the corner. Every date feels like a possibility, not pressure. But by the time many singles reach their 30s, dating no longer feels casual. It feels emotionally expensive. Women in that age bracket often have endured years of rejection, guys who ghosted them, promises that evaporated, and relationships that went nowhere. Now they have to endure being compared with younger women and watching their married friends make bar mitzvahs while they still sit at singles events or wait for a suggestion from a shadchan. To make matters worse, the constant communal message is that their value is declining with age. So yes, sometimes that triggers a need to feel wanted, and thus expectations rise where they want to see a guy go above and beyond his means. I’m not saying it’s okay for a young lady to demand or expect a guy to wine and dine her, but it’s important to understand where they’re coming from. Not necessarily because they are “gold diggers,” but because they no longer want to feel like an afterthought.

A young lady who spent 15 years dating may interpret effort differently than a 22-year-old. To her, a man who planned a thoughtful evening may symbolize seriousness, maturity, and intentionality. She may (falsely) think “If he can’t invest in a proper date, how can he invest in building a life?” You are correct that dating has become financially draining. People underestimate what dating costs men, especially older singles who are dating seriously and consistently. Between restaurants, lounges, parking, tolls, gas, and repeated first dates that go nowhere, a man can easily spend thousands of dollars yearly just trying to find his bashert. Unlike what many people assume, most men are not wealthy. Many are working extremely hard to survive financially while also trying to maintain dignity in the dating world. So, when a man spends $400 on a first date only to receive a “You’re a wonderful person but…” text the next morning, it can absolutely breed resentment. The problem is not necessarily that women are “gold diggers,” the problem is that modern dating has become performative.

Somewhere along the line, people stopped asking if they can build a life with the person they’re dating and instead evaluate their dates like experiences. Was the restaurant impressive and upscale? Did he offer wine and a round of appetizers before the main, and did he also offer dessert? Was there enough chemistry? Enough excitement? Enough entertainment? 

This is what’s going on and people have the chutzpah to express that there are no good guys out there! Men are being imposed upon that they need to impress women through money and upscale experiences because they fear simplicity will be perceived as cheapness. The irony is that women sometimes mistake luxury for effort because emotional consistency has become so rare. Meanwhile, genuine connection gets lost. Hence, the overwhelming number of never-married singles in their thirties, forties, and beyond. 

The tragedy of all this is that something else is happening beneath the surface: burnout. Singles who get older are tired of dating. Tired people become transactional. Men begin calculating dollars spent versus outcome. Women begin calculating emotional investment versus likelihood of disappointment. Suddenly dating stops feeling human and turns into financial scorekeeping. 

You mention shadchanim siding with young ladies. But many shadchanim are responding to the realities they observe. They know many women feel invisible, dismissed, or undervalued in the dating system. At the same time, they also know many men feel financially and emotionally drained. Both things can be true simultaneously, and they should really be objective if they want to help singles.

What also concerns me about your letter is the tone of “we know it’s not our fault.” That mindset cannot be helpful to you or anyone in the long run. Whenever groups of friends gather and reinforce each other’s grievances, it creates an echo chamber. Men convince each other that all women are entitled. Women convince each other that all men are immature or commitment-phobic. Neither narrative is necessarily true.

There are women who absolutely misuse dating for free meals, status, or attention. That exists, and let’s not pretend otherwise. But there are also men who breadcrumb women for years, chase younger girls while rejecting age peers, avoid emotional vulnerability, or expect women to remain endlessly cheerful while enduring uncertainty and rejection. Everyone has complaints; the danger comes when frustration hardens into cynicism. Cynicism is deeply unattractive—in both genders.

Since young ladies are reading this article, this one is for them: I want to challenge the assumption that expensive equals meaningful. Some of the healthiest marriages began with simple dates, long walks, coffee runs, supermarket sushi, or sitting in a parked car talking for hours. True connection cannot be purchased. In fact, some people hide behind extravagance because possessing values that render a good husband and father are harder than picking up a check. Be careful not to confuse effort with spending. A man investing financially is not always investing emotionally. Judge character more than presentation.

My advice to you and other men is stop trying to impress women through money. Impress them through presence, consistency, confidence, kindness, emotional maturity, and intentionality. A thoughtful, well-planned modest date often lands far better than an expensive but emotionally empty one. The young lady who is right for you will share those values, and the ones who aren’t and refuse to go on another date are Hashem’s way of weeding out those who are not meant for you.

Most importantly, both sides need more empathy. Men are not walking ATMs. Not all women are luxury seekers. Most people are simply lonely and scared. Most people are trying not to waste more years of their lives. And when fear enters dating, people often overcompensate, some with money, some with expectations, some with walls, some with demands. The answer is not to blame one gender. The answer is to restore sincerity to dating. Not every date needs to feel like a corporate event. Not every interaction needs to be luxurious, or Instagram-worthy. Sometimes two exhausted people sharing an ice cream, deep in conversation, is worth far more than a five-star restaurant. 

Baila Sebrow is president of Neshoma Advocates, communications and recruitment liaison for Sovri-Beth Israel, executive director of Teach Our Children, and a shadchanis and shidduch consultant. Baila also produces and hosts The Definitive Rap podcast for 5townscentral.com, vinnews.com, Israel News Talk Radio, and WNEW FM 102.7 FM HD3, listenline & talklinenetwork.com. She can be reached at [email protected].