DATING FORUM

By: Baila Sebrow

Question

I’m new to the dating scene as a second time around single. I’m 42 and divorced, and I would love to find a good solid guy. I got married when I was 24, so I had a lot of dating experience before I got married. It was so much more normal back then. I loved going to singles’ programs, and guys were usually honest. Now the guys I meet lie about their age. The 60-year-old men lie and say they’re in their 40s. The guys my age are looking for 20-year-olds. The guys at Shabbatons are not serious about marriage; they just go to have a good time. The women that go are serious about getting married, but they end up wasting money and their time meeting men who are not serious. I’d rather just go away somewhere with a few friends. At least then I don’t get disappointed. I’m sure you’ve heard all this already.

The regular evening events are not much fun either. Can you tell me why nowadays events are segregated according to hashkafa? And also, why are events segregated by the words “divorced” or “single”? Singles that were never married are called “single.” And divorced people are now called “divorced.” Divorced people are single too! Some events for the divorced are just for people who have no kids. I could write more, but you get the idea. Where can I just find a good solid guy without all these mishugasen? Do they exist?

Response

You’re speaking my language! I have been shouting your words practically from the rooftops! As a shadchan organizing events for so many years, I will never subscribe to these New Age methods you mentioned because they yield more aggravation than success for singles. I cannot control what other organizers do, but because it hurts me to watch what’s going on, I call out what I feel is wrong whenever I see it. Moreover, what you’re describing is something a lot of never-married and second-time-around singles feel in the frum world right now. Please know that your frustration is felt by most singles, even the ones who stay silent. Thank you for articulating your thoughts so eloquently and bringing them to the Dating Forum.

The shidduch culture has drastically changed over the last 15–20 years. When you were dating in your twenties, there was generally more social mixing of hashkafos, less branding, less “market positioning,” and less obsession with categories. Events were designed in a way to allow people to meet more naturally. That’s why it was common to find singles from completely different hashkafic backgrounds marrying each other and building the beautiful families we have today. Singles’ events then were all about creating a venue for singles to meet rather than implementing an agenda. I’m not saying that the organizers’ basic goal of getting singles to meet each other for marriage has changed today. Actually, the more singles that meet at their events and get married is how one can gauge their success. What has changed is that many events now feel transactional and performative under the guise of being curated.

A few things are happening at once. Hashkafa became more segmented socially because communities have become more insular and identity-driven, so organizers market events narrowly because people self-select that way. With regard to second time around singles, divorce carries logistical realities: children, ex-spouses, schedules, geography, and finances, so organizers separate groups thinking it creates “shared life stage” compatibility. But truthfully, that’s not something the organizers need to get involved with. Rather, that’s for the dating participants to figure out after they meet each other at an event and want to take it a step further, just like in years past. Even today, there are never-married singles who would date a divorced person with kids. Organizers should not act as judge and jury when they organize an event by deciding who gets to date whom. But what’s really happening is that many events survive financially by selling hope and volume, not necessarily by creating meaningful matches.

Men and women often experience these singles events differently. Women frequently come hoping for sincerity, clarity, and the chance to meet (as you described) a “good solid guy.” Some men come open-minded; others come for validation, attention, socializing, or an ego boost. I’m not saying that years ago there weren’t such men like that, but if they attended an event organized by a shadchan, they took it more seriously. Now there are men who outright lie to shadchanim. The other problem is that the online dating culture bled into frum dating culture. That brought about endless browsing, age filtering, unrealistic expectations, and people often misrepresenting themselves.

And yes, the age issue frustrates many women. A 60-year-old man saying he’s in his forties isn’t just annoying; it breaks trust before a conversation even starts. At the same time, many decent men in their forties and fifties are also discouraged because they feel invisible unless they’re wealthy, flashy, or unusually charismatic. The whole system can make normal, grounded people feel overlooked.

We cannot change how some organizers design their events, nor can we change the behavior of certain men. But here’s the important part as it pertains to you. The events themselves may simply not be your environment anymore, but that doesn’t mean there are no good solid men.

From what you wrote, you sound like someone who wants honesty, emotional maturity, stability, and sincerity in a man. You come across like a very grounded young lady, and you most likely feel compatible in a relationship that feels calm rather than performative. The men who fit that description are often not the loudest or the most noticeable people at singles’ events.

What I typically advise women in your position to do is to try other types of environments to meet marriage-minded men where they ultimately often have better experiences. Smaller Shabbos meals through friends instead of organized Shabbatons can feel more relaxing and personality-oriented. Hosts typically invite guests that would be comfortable sitting at the same table with each another. Try reaching out to married people and inform them that you want to remarry and are looking to meet someone compatible. Introductions through married friends who actually know both people usually produce excellent results. You might also want to try volunteer opportunities where people repeatedly see each other naturally while enjoying doing a mitzvah, such as bikur cholim in hospitals or rehab facilities, or other charitable organizations that bring volunteers together.

You did not mention what you do for work, but there are professional and social organizations that offer classes, lectures, community projects, travel groups, and chesed organizations within certain fields. I would also recommend reaching out to carefully vetted matchmakers who work with second-marriage daters, specifically those that value personality over résumé categories. And honestly, your instinct about traveling with friends instead of spending money on disappointing events makes sense. Sometimes people meet someone organically when they stop forcing themselves through systems that feel draining.

One thing I would encourage you not to do is conclude that all men are not serious, or that all guys want 20-year-olds. Some do. Most don’t. There are men in their 40s and 50s who are quietly looking for exactly the way you present: a warm, emotionally-intelligent, stable woman who’s realistic about life and wants a compatible, trustworthy man and peaceful home. Many of them are exhausted by the same nonsense you are.

The question is not “do they exist?” You should be asking yourself, “How do normal people find each other when the dating culture rewards fakery and image?” Often the answer can be found in smaller circles, slower introductions, less marketplace energy, and more real-life human interaction. Also, one thing you said that stood out: “I’d rather just go away somewhere with a few friends.” That sentence tells me you already know something important about yourself. You value authenticity and emotional comfort over spectacle. That’s actually useful information for dating. It means you probably won’t thrive in environments built around mass mingling and superficial impressions. You may do much better in quieter, relationship-oriented settings where people can actually talk and get to know each other gradually. And for what it’s worth, many second-time-around marriages that work well start later, slower, and are far less “exciting” than first marriages. They’re often built more on steadiness, compatibility, humor, kindness, and emotional safety rather than image or fantasy. n

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].