I’m running into another issue. When is the right time to call people like this? We’re veering into post-lunchtime. I kept away from mornings because people are probably out at work. If it’s a young couple with kids, maybe 2 p.m. is a good time? If it’s an older couple, maybe this is afternoon nap time? In the evening, it’s bedtime for kids.

Is there such a thing as etiquette when you’re doing something incredibly socially off?

SIXTH ATTEMPT: “Hi, is this Bracha?” Yes! It’s a young family — I can hear the kids. I stumble through my intro and ask if I should call some other time, but she’s curious what this assignment is.

“Oooh, so cute!! Wow. Ummmmmm, no, I do not have any interesting shidduch stories. Not my siblings, friends, neighbors, nope.”

I ask if I should call later (trying not to sound hopelessly desperate); maybe her memory will produce something? No, if she didn’t think of anything now, she won’t have anything later….

SEVENTH ATTEMPT: No reply.

My poor, poor phone book starts looking like a sieve. Kid One is still enjoying this. I should really stop, but nothing gets me going better than the thought of having to quit. I wait till evening.

EIGHTH ATTEMPT: Again, a cellphone number for a couple. I dial. A man’s voice answers. Hi, can I please speak to Tamar?

“Mah?” (switch to Hebrew)

“Can I please speak to Tamar or have her number?”

“Who??”

I feel like I’ve been dating eight suggestions that have gone nowhere. I need a break!

Okay, ten tries, and that’s it. No more poking the phone book.

NINTH ATTEMPT: The phone RINGS. A kid ANSWERS. I ask to speak to their mom. They ask who it is. Oh. Um. How to explain this?? “She doesn’t know me.” Wait for the kid to hang up on the crazy person, but no! Shoshana is on the phone.

I launch into the intro and wait for her to tell me she has nothing.

“Yeah, I have a story.” I almost faint. Then I run to get a pen and notebook.

Shoshana’s story:

Rebbe Nachman made our shidduch.

The year I turned 19, my father arrived back from Rosh Hashanah in Uman, glowing. He’d met a friend that he hadn’t seen since their yeshivah days, and they’d spent Yom Tov together, catching up and reminiscing. Also… his friend had a son. And my father had a daughter. And after talking about it for two days, they both decided it would be the most wonderful match. I was less convinced. The boy was Israeli. As an American, my Hebrew was rudimentary at best. No issue, my father insisted. The boy knew a bit of English and Yiddish, and I knew a bit of Hebrew and Yiddish. Enough to start off with….

All the insistences in the world wouldn’t convince my father to give up on his grand idea. In a few weeks, I would be traveling to Israel anyway for a cousin’s wedding. What better time to arrange a meeting? Eventually, I agreed, only to make my father happy. I knew it wasn’t going to work. Marrying an Israeli, living in Israel? Not in my plan at all.

I met him once, then flew home, asserting that he wasn’t for me.

Except… the days went by, and I kept thinking of the boy I had met. How he was exactly what I was looking for. I tossed and turned, drove myself and everyone else crazy. Was I right to say no to such a good match? Were my reasons enough? Yes, no, yes, no.

A couple of weeks later I was on the plane again. Destination: Israel….

Mazel tov!

And… it was a match! Somehow, my quest to find someone with a shidduch story feels more complicated than this real one!

*Besides Rebbe Nachman, all names and identifying details have been changed. Come to think of it, I should have changed mine, too. If you are a shadchan, please don’t judge — I do act normally most of the time.

Strike Three and… You’re (Going) Out

Dassi Weishaut

I

’m a youngest child. That means I’m charming, popular, modest, and I love to talk. My sister clearly recognizes this in me, because she texted me this challenge with the comment this seems like something you’d do.

Oh, absolutely. I immediately called three phone numbers and got not a single response, probably because it was 11 a.m. and not everyone works from home. And I wasn’t going to leave messages with strangers like, “Hey, I’m looking for a shidduch story, give me a call.” This was Lakewood, and I’d never get my son into cheder if news spread of the crazy lady cold-calling strangers for dating stories.

Fine. I waited until later in the day and called the next number I pricked. A man picked up, which was already reason enough to hang up.

“Sorry. I think… I think this was a wrong number.”

“Dassi?” he said.

Okay, that was creepy.

“Who is this?”

“You called me.” He was starting to sound annoyed. “If this is one of Dovid’s pranks, it’s a weird one.”

Okay, so he knew me and he knew my husband. And come to think of it, he did sound kind of familiar. Had I somehow, out of all the people in the local phone book, picked someone I knew? This wasn’t exactly a small town.

“Who is this?” I repeated.

A sigh on the other line. “It’s Baruch. Did you mean to call Rina?”

I… did not have my brother-in-law saved in my phone. And to be fair, my married name (which will remain anonymous) is a very common one. I hadn’t made the connection, and now I was about to have a very awkward conversation.

“Is Rina around? I was actually looking for a shidduch story. It’s for this challenge — my sister writes for Family First…”

As it turned out, Baruch had a story to tell me, one that I’d never heard from him or Rina before.

His sister Bryna was 15, and the only kid still living at home. They didn’t have the most stable home life, which I guess a lot of local people knew, so when Mrs. Trachtenberg spotted Bryna at shul a few times, she decided to take Bryna under her wing. She had a few girls around Bryna’s age, and Bryna became a bas bayis there, happy to have a safe space.

A few months passed, and Bryna mentioned casually that she had a brother in Milwaukee of marriageable age. Mrs. Trachtenberg immediately perked up.

“Tell me about him,” she ordered Bryna.

The next day, Baruch got a call.

“Hi, this is Mrs. Trachtenberg. You probably don’t know who I am. I just found out that you exist. But I have the perfect shidduch for you!”

Baruch had heard the name from Bryna once or twice, but he was taken aback — to say the least.

But before he could say a word, she launched into a description.

“She’s a girl from Lakewood.” Strike one. “She’s a Litvak.” Strikes two, three, four, five, six, seven, eight, nine. “She’s two years older than you.” Strike ten. Baruch was not going to date this girl.

But he didn’t have any other dates at the time, and his rebbi said, “Why not? Go out with her — you have nothing to lose.”

Baruch conceded, but he was firm on one thing — he was not going to Lakewood for a date that wasn’t going anywhere. She was welcome to come to Milwaukee, but he wasn’t traveling for this.

Mrs. Trachtenberg relayed the message and got a similar response from the girl — if Baruch wasn’t willing to go to her, then she wasn’t willing to go to him. But Mrs. Trachtenberg pushed her. Maybe she had a sense about this shidduch. Maybe she was, like so many of us, just throwing things at a wall and seeing what stuck. Whatever it was, the girl booked tickets to Milwaukee.

While she was doing that, Baruch realized that Chanukah was coming and he hadn’t been back in Lakewood in a year and a half. He figured that he might as well go for Shabbos Chanukah and see his family (which didn’t yet include me). Baruch called Mrs. Trachtenberg and let her know.

At this point, the girl was fuming at him. What kind of game was he playing? Was this some sort of power play? “He can come to Lakewood, but I’m not going out with him in Lakewood,” she shot back. “I have nonrefundable flights, and what happens if it doesn’t work out?”

Mrs. Trachtenberg talked her down. “Go out with him,” she assured her. “Worst-case scenario, you’ll push off the flights and go on vacation another time.”

So Rina and Baruch went out a few times in Lakewood. A week later, they went out a few times in Milwaukee. A week after that, Baruch was back in Lakewood to go out with her a few more times.

And the rest is history.

Clearly Off-Target

Erin Stiebel

I

was a bit wary of who my pin would land on in the local neighborhood phone directory. It was a relief when it dropped on Zahava Green*, a cute newlywed with an easy laugh and a perpetual twinkle in her eye who would hopefully still have some fresh dating stories in her back pocket.

“Hey, Zahava! I know we’ve bumped into each other at the grocery store before. One of these days, we’re going to have you guys over for Shabbos. In the meantime, I’m writing this article for Mishpacha. I just have to know — do you have any crazy dating stories?!”

Zahava didn’t miss a beat. “Do I only get to share one? Skip the article. Let’s publish a book!”

Oh, yes, I had scored the best case study. Baruch Hashem.

Zahava unloaded some of the greatest dating stories I’ve ever heard. I was doubled over with laughter, crying from the cringe, and begging for more. (You only get one today, but maybe we’ll share more in the future, dear readers!)

Ladies, I present you with Zahava’s dating adventure:

Growing up in an out-of-town Sephardi family, many of the names I received were just other out-of-town Sephardis, regardless of whether or not they were shayach. So when I met Rachamim for a date in New York City, I knew I was in for an experience.

I was newer to dating, and I tried very hard to be the sweet, eidel girl that the shadchan had sold — easygoing and compliant. The lot where Rachamim had parked was a bit far from the hotel lobby he had chosen. No big deal. I was sure I could handle anything.

“I see you’re wearing heels,” Rachamim noted. “Will the walk be okay for you?”

Look at those middos, I thought. Aloud, I said, “These heels? I could run in them!” Look at me, being so low-maintenance!

“Oh, yeah? Prove it.”

And before I could respond, Rachamim was sprinting down 34th Street.

And I mean, he was my date. What could I do? I threw up my hands and ran after him.

Eight blocks later, my foundation dripping down my face, we arrived at the hotel lobby.

“Guess you can run in them,” he said casually.

He chose the sofa directly in front of the reception desk, ordered us two glasses of water (gotta hydrate after a workout) and, like our little jog was the norm, dove into the date as if we had just arrived by — I don’t know, here’s a radical suggestion — car.

As he peppered me with the usual first-date questions, I tried to daintily dab my sweaty face with the incredibly small napkin that accompanied my glass of water. But the surprises weren’t over yet.

After several minutes of sharing how inspired I always am by Bais Yaakov productions (leaning into eidel, easygoing, first-date Zahava), he interjects, “Do you want to take a break?”

I paused. Wait, what?

“Excuse me?” I laughed uncertainly.

He wasn’t deterred. “Do you want to take a break now, in the middle of the date?” he repeated.

“Um, sure. I guess I’ll go to the restroom?” I said, bewildered.

“Great, it’s down the hall.” And with that, we parted ways.

I waited in the restroom until I imagined recess was over. When I returned, he was in the lobby, removing his coat and sitting back down at the inconveniently placed reception desk sofa.

The conversation continued without mention of the break, where he went, or why it was requested.

It was clear that, while Rachamim did get me a glass of water after our run, he was not someone I’d continue dating. So on the ride home, I decided that if he could call a break on the date, I could ask a question I’ve always wanted to ask on a date.

“Rachamim, what’s one thing you would never share on a first date?”

We had just arrived at my house. He put the car into park and looked right at me.

“I’ve never told anyone this before, but… I used to make illegal buy-one-get-one-free coupons and use them at Target. I stole from Target. And then I got caught. And now I’m banned from all Targets everywhere.”

I picked up my jaw and my bag and used my running heels to sprint into my house.

Goodbye, Rachamim. I know where I’ll be shopping to avoid any future run-ins.

A Rabbi, a Priest, and an Imam…

Shoshana Gross

IN

a small town out in the Midwest, where the corn grows thick and cows roam the streets, I gaze at the phonebook.

Mission: Stick a pin in the phonebook and find a random stranger to ask for a good shidduch story.

Problem: Our phone book is four pages long, and since it’s printed double-sided, that means that I’m holding what’s essentially a folded piece of paper. And finding a stranger isn’t going to be so simple, either — even though when you work from home as a writer, you spend more time with your computer than living, breathing human beings.

But… time to take the plunge.

I stick the pin into the page and wince at my first choice. My kids’ principal. No, not happening. Try Number Two nets our around-the-corner neighbor. Strike two. Number Three is a friend who lives a few blocks away, and I realize that this is going to be harder than I thought.

Attempt number four is the charm. Benjy and Baila Marks? I’ve never heard of them, never met her at a kiddush, never saw the name on any of my kids’ class lists, and she definitely isn’t my neighbor.

After a little phone tag, we finally connect.

I introduce myself and relay my odd request. “…so I need to call someone I don’t know to ask for a shidduch story, and I picked you,” I tell Baila. “I don’t think we’ve ever met.”

She’s gracious and doesn’t hint that I’m insane (which I appreciate).

“That makes sense,” she answers. “We moved here after our children were grown, and I don’t get out much.” It turns out her husband davens at the other shul in town (we only have two), which is why I never met her at a kiddush.

“Do you have a shidduch story for me?” I ask.

She launches into her tale:

I grew up in the tristate area, and I have a brother who has an unusual combination of names. He’s called Menachem Meir, and every time I would tell people his name, they’d correct me — “Don’t you mean Menachem Mendel?” (As if I didn’t know my own brother’s name.)

One Shabbos, my father was in shul when a visitor was called up for an aliyah — Binyamin ben Menachem Meir. His ears pricked up at the familiar, unusual combination, and he first noticed the young man who would be my future husband. Benjy was spending Shabbos with a local friend, but my father didn’t get a chance to speak to him before he left.

A few months later, Benjy was revisiting his friend for Shabbos. After davening, he told his friend a great joke.

“You have to tell that joke to Rabbi Brecher!” he said, pointing to my father. The shul was small and warm, the kind of place where every mispallel knew each other well enough that he knew my father would appreciate the joke.

Benjy went over to my father, introduced himself, and shared the joke. My father remembered Benjy from his aliyah a few months earlier, and the two of them schmoozed for a while.

When Benjy’s friend finally came to collect him, he left my father deep in thought.

“What a nice bochur,” he mused. “And what a great joke!” It suddenly hit him as he left shul. “I think he would be an excellent shidduch for my Baila.” He didn’t waste any time, and soon, the shidduch ball was rolling.

It wasn’t long before the two of us were the quintessential glowing chassan and kallah, celebrating our vort. Between the streams of visitors and a flurry of mazel tovs, my father proceeded to pull a wad of bills from his left pants pocket and ceremoniously deposit it in his right pants pocket.

“What are you doing?” someone wanted to know.

“I’m paying the shadchan,” my father explained, amid chuckles from the appreciative crowd.

Years later, my husband still says this story at our Shabbos table, and he always ends with the same line — referring to my father: “I told the joke, but the joke’s on him!”

I once asked my husband, “What was the joke you told my father?”

“You know, I can’t even remember what I said.”

Was it a knock-knock joke? (Unlikely). A clever pun? (Who nose?) A witticism along the lines of “A rabbi, a priest, and an imam”? (Raising the bar a bit…)

We’ll never know exactly what joke he said. And I don’t think my father remembers, either. But I’m glad he said it.

Busy? Bashert!

Bashie Lisker

I

wasn’t planning on doing this challenge. (And I definitely heard from a lot of writers who felt the same way). It’s possible we’re a solitary bunch, holed away in our houses and hunched over keyboards, afraid of speaking to strangers.

But the truth is? I quite like talking to strangers. I have no sense of shame or self-consciousness there. Honestly, I’d be a fabulous telemarketer or fundraiser if it didn’t break one of the four yehareg v’al ya’avors (Avodah zarah. Gilui arayos. Shefichas damim. Being annoying). And I was very tempted by this game.

So I pulled out my local directory and stuck a thumbtack through it. Pretty aggressively, actually. I thought I might get a couple of phone number pages after the ads, but as it turns out, I punched that tack right through the entire thing. I had lots of options.

The first name I stopped at just listed a woman. Excellent. I imagined an older woman who had lived a long life full of wacky shidduch stories and called her up.

I heard kids in the background. Young ones. “I’m collecting shidduch stories,” I said, bright and sunny.

“Well, mine didn’t end great,” she said ruefully. Oh, no. No other stories came to mind, either, so I went on to the next pinprick.

This one was a lovely woman named Debbie who shared a beautiful vignette with me. Before she and her husband had become frum, they’d met in a Reform singles’ group in North Carolina. Debbie had been very involved in the group after her marriage, too, and she’d singled out one divorced man and one divorced woman. “They were both around the same age, they were both nice, and what did I know? I introduced them, and they got to know each other.” They had both been dealing with children going through some issues, and they had gotten closer and eventually gotten married.

Debbie told me a little bit about her journey of becoming frum, too, and her travels from Pittsburgh to New York. It was nice getting to know her — our only neighborhood interaction until now dated back to the food distributions during Covid, when I had more milk than my family ever needed and was looking to give it away.

But I was on a roll now, and I was hunting for more strangers. I flipped to the next page, and my eyes lit up. It was Shira*, a friend from the neighborhood. Shira would take my magazine demands in stride, I was sure. And she was the kind of person who knew everything, all the time, the most reliable person in the entire neighborhood (I hope I’m not outing her here! I suspect I am). There was no way she wouldn’t have a great story for me.

First, she told me about a nightmare date she’d been on. The boy had picked her up for a second date, heading to a Dave and Busters-style place in the city. But he drove in circles, around and around, and there was no such place anywhere near where he insisted it would be.

“That’s fine,” he decided. “We’ll just go somewhere else.” The next entertainment he found was a mini-golfing place. Which might have been nice — I remember doing that with my chassan, back in the day — except that it was getting late, and it was raining. Shira juggled the golf club and her desperate efforts to protect her hair.

The good news was that there was no one else at the mini-golf place, so they were able to play in record time. The great news was that Shira would not be racked with indecision about going on a third date with this boy.

At the time, Shira worked at the local JCC, which was full of young frum girls and at least one budding (older) shadchan. While commiserating with another girl about their dates, the girl said, “Honestly, mine wasn’t for me, but he seemed like a really nice guy. A smart guy.” And as these things go, she said, “Wait, Shira’s nice and smart. Let’s try this.”

Shira’s family reached out to the shadchan, and they were told, “Oh, no, he’s busy.” He had just gone out with her friend the day before, but sure. Boys in shidduchim.

After a few days, on Tuesday, the shadchan called Shira. “He’s interested. Can he call you to set up a time?”

That had escalated quickly from busy. “Can we check him out first?” The shadchan was a little put out at this. The nerve of Shira, not checking out the busy boy just in case! But her mother made the calls, and Shira finally reached out to the shadchan again on Wednesday and told her that she was interested, too.

On Thursday morning, the shadchan called her. She just wanted to let Shira know that the boy was busy again.

Shira was flummoxed. “What do you mean? You just told me Tuesday that he was willing to go out. And on Wednesday, I told you that I was interested!”

“I don’t remember that,” the shadchan said disapprovingly.

Shira hung up, at a loss. She really had been interested in this boy. He had sounded like a perfect fit. But clearly, it wasn’t meant to be.

She took a breath and tried to center herself. This was out of her control, she decided. She wasn’t going to get upset, and she was going to accept that this was all part of Hashem’s plan for her. There was that temptation to vent to her friends, to resent this boy, but she tamped it down. What will be, will be.

An hour later, the shadchan called her again. “He’s available,” she announced, in possibly the quickest busy-not-busy turnaround of the century. “He’s going to call you tonight.”

And as Hashgachah would have it, he was nice and smart, and so was she, and Baruch Hashem, they’ve been happily married for 21 years — despite a hapless, mildly confused shadchan.

(Originally featured in Family First, Issue 973)