| Family Tempo |

Choose Your Own Shidduch Adventure

Another first date. This time you can choose what happens next

It’s 5:52. You didn’t include the 20-minutes traffic in your down-to-the-minute plan, but you’ll still have enough time to prepare quickly. You already know what you’re wearing tonight — the same thing you’ve worn to every other first date this season.

By the time you dash through the door and up the stairs, you only have four minutes left for dinner. Your mom follows you up to your room with a piece of schnitzel in a paper towel.

She kindly doesn’t say, “I told you so,” even though she clearly doubted you when you reassured her this morning that no, you didn’t need to leave work early. But even the breathless rushing can’t overpower the soft voice that pipes up before every date. Maybe this time… maybe it’s him.

By 6:45, your hair is softly curled and you’re clacking over to the mirror to touch up your lipstick. You’re ready with a full 15 minutes to spare. (Heard that, mom?) You even have a couple minutes for some Tehillim and a few “have me in mind” texts — and to find your ever-trusty dating clutch.

You dig for it under a pile of shoes. You search under your sweaters. Nothing.

What now? You smush a $50 bill into your shoe and slip it back on. Just in time for the knock at the door.

Five minutes later, the date officially commences with his, “So, how does Sun & Sea Hotel sound?” and your “Sure, sounds great.”

But as you leave your neighborhood and the awkward small talk picks up speed, so does the rented blue Camry. It’s getting a little hard to focus on the conversation, because you’re too distracted by the speedometer.

And by how uncomfortably close you’re getting to that red car.

And by the third turn in a row that was executed with a tad too much gas.

You distinctly recall one of the rules in the Unwritten Handbook of Shidduch Dating (passed verbally from friend to friend): Never EVER comment on the way your date is driving (at least not until he proposes).

But you’re starting to feel a bit queasy and, besides, you want to come home in one piece.

Do you follow the rules and stay silent (2) or go with the psak of Chayecha kodmin and comment on his driving (3)?


You watch the street lights flash by and hold on to the side of the seats. But as fast as your heart beats — and as much as you value your safety — you bite your tongue.

You know what will happen if you do speak up. Your façade of a sweet and obliging potential future wife will shatter as quickly as your windshield will if he doesn’t turn RIGHT NOW to avoid the oncoming street pole.

So you take a deep breath and close your eyes. You barely hear him ask, “So where do you work?” (Even though you both know his mother read your résumé and filled him in on precisely what your role as project manager entails at Bergman and Co, where you’ve been working for 2.73 years, and where the references listed on your résumé find you “Pleasant, accommodating, and sooooo capable….”)

“Hmm?” you say. He looks over to see if you’re okay — or at least you assume he does (you don’t know for sure because your eyes are closed), because he asks, “Are you okay?”

You pry your eyes open and exhale when you see the hotel sign just down the road. “I’m fine!” you say — a little too enthusiastically, but baruch Hashem your sister isn’t here to tell you off for using your high-pitched I’m-faking-excitement voice.

“My friend told me about this place,” he explains. “It’s officially really nice. And the best part is that barely anyone knows about it. It’s always good to find a new place.”

You hold back a smile. You know exactly how nice this place is — there are tons of couches to choose from, the Coke is never flat, and the waiters generally leave you alone. In the barometer of not-bad dating places, this one scores high. You know this because you’ve been here before. Five times.

Your date slows down outside the parking lot. “I wonder how we get in,” he says aloud. You know the entrance is right down the block, hidden by a patch of trees. It’s not his fault he can’t find it. Most people miss it— the last two guys who took you here definitely did.

You play with your rings and deliberate:


Should I show him the entrance and admit that I’ve come here on a date before (5)? Or bite my tongue and let him circle until he finds it (4)?


As you merge onto the parkway, you see your chance.

“So,” you say with perfect nonchalance, “what does your family hold about Tefillas Haderech? Do you say it on short trips like this?” Before he has a chance to answer, you continue. “My personal practice is to be machmir in this area.”

Either he got the hint or you’ve gotten used to it, but either way, there seems to be some improvement. Enough that you can unclench your fists and open your eyes.

You make it to Sun & Sea after a record-breaking three rounds of Jewish geography. Including, but not limited to: “So, where in Flatbush do your aunt and uncle live?… Oh, that’s just around the corner from my cousin… But yeah, New York, they probably don’t know each other.”

You also make it through two awkward pauses, and one offer from the Unwritten Handbook of Shidduch Dating, guys’ version: “Make yourself comfortable. Are you cold? Feel free to change the temperature.”

All seems to be cruising along until you pull up to the parking meter. Your date reaches into his jacket pocket for his wallet. Not there. He checks his pants pockets. Then, “Uh… I think I left my wallet at home.”

With a reassuring and carefully nonjudgmental smile, topped with understated grace, you bend down in a tzniyusdig way that would make your fifth grade morah proud, slip off your shoe, and withdraw a crumpled 50. (Your mother will be so thrilled that her advice finally came in handy.)

“You can use this,” you say. He turns red. You turn away. But he recovers nicely and says, “Shoe, that was close!”


You graciously manage to pick up the conversation where you left off. Good for you! Go on to 6.


You lean back in your seat. If you’re going to be here for a while, you may as well be comfortable. You wonder how long it will take. Two guys ago, it was nearly ten minutes of circling. The last guy got it after five — but he’d rolled down the window to ask a passerby for help.

“I still can’t find the entrance,” your date reiterates. You almost consider putting on that sweet voice and saying, “I’m totally not sure, but I think that like it may like be that way…” Even if he does catch on that you’ve been here before, maybe he won’t realize it’s the fifth time.

Instead, you nod along when he asks, “Mind if I call my friend to ask for directions?” As he picks up the phone to dial, a car pops out from between the trees, revealing the entrance for all to see.

“Ah! There it is!” He floors the gas and zooms into a spot. You unclick your seatbelt, smile at him, and swing open the passenger door. Finally, you’re there.


Continue to 9, and remember to keep up the charade when it’s time to look for the restrooms.


“So… I think it might be that way,” you say. “Like, that looks like it might be an entrance, no?”

“Good point, let’s try that,” he says, swinging the car in that direction. Your prediction turns out to be spot on. He glances at you sideways with suspicion.

As the two of you walk through the huge revolving door (in separate sections, obviously), you promise yourself that you’ll give this date your all. Even if I did come here just three weeks ago. And two months before that. And a month before that, and three months before that. And had a similarly-fascinating conversation about the merits of bottled versus tap water. With another guy. In the same tie. They’re probably roommates.


You resolve to give this date your all, and to give this guy a fair chance. Even if he is wearing a purple tie. Points for you! Continue to 6.


There’s a piano in the center of this upscale lobby.

“Is your family musical?” you ask, a fleeting picture of your dream Shabbos table appearing in your mind.

“We like singing, but none of us actually play anything. Why? Are you into music?” he asks. After hashing out each of your favorites, from Mordechai Shapiro to Ishay Ribo, you find common ground: Abie Rotenberg. (And proceed to dissect every song on his Journeys albums — but not “The Shadchan.” You stay far, far away from the “The Shadchan.”)

As you both grope for the next not-too-heavy, not-too-inane conversation piece, you glance around the lobby. This supposedly secret lounge is currently hosting three frum dates. Not that you’re staring — it’s just that guys in suits and girls in heels stand out in a hotel lounge almost as much as they do in a Wegmans.

Suddenly, you gasp in shock. No way! Another couple just walked in — and the girl in the midi chiffon skirt is definitely your friend Leeba (that’s her first date outfit). How’s her date going? You’re itching to find out.

Behave yourself, the combined voices of your mother, teacher, and the shadchan say firmly in your head. First impressions count.

But shouldn’t he see that I have friends?


Do you ignore her (7) or wave and execute your “if we ever meet on a date” plan, which involves escaping to the bathroom exactly 17 minutes after you first bump into each other (8)?


With a twinge of longing, you bat away your inner teenager and try to refocus. “Sorry, what’d you say you usually do in the summer?”

“The last two summers I went on SEED.”

You perk up at this. Yay, something you don’t already know from his résumé!

“Wow, what’s it like?”

“It’s really geshmak!” He grins, leaning back on the blue armchair cushion. “We had a learning seder in the morning, ran the day camp for an hour or two — every day we tried a different cholent recipe with the kids — and I can’t say I minded having grilled chicken and steaks every night! Actually, that guy was with me in Montana!” he says, waving at the bochur who’s passing by — with Leeba.

Leeba does a double take when she sees you. I’ll tell you later, she says with her eyes. And they head off, trying to find a spot that’s not too close to the bar, or to the other frum dates, or to the huge screen broadcasting a football game.


You scored major kibbud eim points for behaving so nicely. Go directly on to 9 — and maybe get a nice cold hotel Coke as a treat on your way.


Exactly 17 minutes later, you grab at the opportunity that the lull in conversation offers you to excuse yourself. “Uh, I’m just going to, um, go,” you say, gesturing in the general vicinity of the restrooms.

You swing open that blessed brown door that says Ladies and wonder why they’ve yet to rename it Place of Refuge. 9:34… 9:35…

The door opens twice but it isn’t Leeba.


Just as you’re about to give up, Leeba finally glides in and explains, “He went to the bathroom a few minutes ago so I couldn’t leave before he came back. I saw it was 17 minutes, but I felt bad about him coming back and having no idea where I disappeared to, so I finally wrote him a note that I was going to the restroom and I’ll be right back.”

“You’re excused,” you say. “But where on earth did you get a pen and paper?”

“You mean ketchup and a napkin?” Leeba asks. “From the bar.”

“Brilliant! Did you make a smiley face with the mustard too?”

“Of course. Nu, should we start looking for gowns?”

“Oh, shush,” you tell her, then glance at your watch. “We should head back — unless you want to call an Uber and ditch them instead?”


Knowing no shadchan will set you up again if you date and dash, you and Leeba leave the bathroom — one at a time. Head straight to 10. 


“So…you’re in BMG?” you ask during a lull in conversation. You swirl your Coke with a straw and mentally kick yourself for asking. Of course you know he’s in BMG. And he knows you know already.

“Yep,” he nods.

“Which building do you learn in?” you ask, not that you really know the difference.

He says that he started in the Yoshon, but this zeman he’s in one of the newer buildings.

“I wonder who else I know in those buildings,” you wonder — out loud, unfortunately.

“What, like other guys you dated?”

You turn red. “I mean, uh, my cousins.” To change the topic, you quickly reach for your glass and take a sip of Coke. It’s empty.

“Um, is it okay if I get more Coke?” you ask.

“Of course, of course — I’m so sorry I didn’t offer!”

“It’s okay, really,” you say for the third time in a row.

“I’m sorry,” he repeats as he walks away.

“Don’t worry,” you wave it away, wondering which rule from the Guys Handbook he’s broken.

You watch your date walk back to the bar. He speaks with the waiter and hands over your empty glass. Moments later, he’s back at your little corner of the lobby, apologizing again.

“It’s totally fine,” you reassure him with a warm smile. And as you settle back into the conversation you realize that, with the right guy, anything is.

“How about some air hockey?” your date asks. He gestures to a side room off the lobby, where an air hockey table stands in all its glory.

“Sounds like fun,” you say, and follow him across the room. You take your places across the table and get ready to begin.

What your date doesn’t know yet is that you’re invincible at air hockey. Truly. You’ve won every single game you’ve ever played — which isn’t actually saying much, considering that most of your siblings are too scared to play with you. Are you ready for your date to see you like this? Competitive? Motivated? Fierce?


Should you lean into the competition and try to win (12) or play nice to save your date the trauma of seeing your inner Olympian unleashed (11)?


One more bathroom break and 19 topics later, you notice the early beginnings of a headache. You peek down at your watch. 10:10. From the way he’s leaning back and the very long, detailed story he’s telling, it’s clear he’s in no rush to get going.

You shift in your seat. You bite your cheek to suppress a yawn. You feel your mascara dripping and wipe under your eyes with your finger. You shift in your seat again and listen to the climax of his story. Would you believe it? There was a Chabad house just five minutes from where the rental car broke down. What are the chances?

Your headache is getting worse, you’re tired, there’s still a 30-minute drive home, and apparently — unfortunately — there’s a whole ‘nother chapter to the story. You want to go home, but…


Do you tell him straight out and throw away the centuries-old tradition, passed from bubbe to mama, that he must decide when the date ends (14) or continue to languish in pain and exhaustion (13)?


You realize there’s no choice to make. Your date is scoring so badly that you’re going to win — even if you try to lose. You remember your brother telling you that guys always try to let the girl win and wonder if he’s purposely trying to lose.

When your date lets an easy save pass him right by, you know the answer: “You’re losing on purpose,” you scold, gesturing with your pusher. “It’s no fun this way.”

“What do you mean?” your date asks. He’s genuinely confused. Is it possible he wasn’t playing badly on purpose? That he’s actually this bad at the game?

You mumble “never mind” and push the puck back to his side of the air hockey table. Only two more points until you win anyway, and then you can head back to the lobby — whatever kind of consolation that is.


Remind yourself that air hockey prowess isn’t  part of your response when they ask, “So, what are you looking for?” and continue on to 10.


I may as well have fun, you decide as you eye the goal. With one strong push, the puck goes flying across the table. “Ouch!” your date shouts when it hits his fingers.

You gasp and cover your mouth. “Omigosh I’m so so so sorry.” Should you ask if he’s okay? Or is that too personal?

“I should have warned you,” you say instead. “When I was in third grade, my brother broke his finger playing with me.”

Your date chuckles as he holds the injured hand in his other. “I can imagine why.” He looks at his finger and then declares that nothing’s broken. “Ready to continue?”

“Are you sure?” you ask in a timid voice.

He takes his stance again and pushes the puck back across. “Yeah,” he says. “I’ve never lost a game of air hockey — and this is definitely not going to be the first time.”

“What’s so funny?” he asks when he sees you laughing.

“Nothing,” you say. I’m just realizing that you’re possibly the coolest guy ever.


When you get home and tell your parents you sorta enjoyed, they’ll start planning a l’chayim. That’s why you need to go to 16.


Forty-five minutes later, he finally says it. Those magic words. “Should we get going?”

“Yes,” you stand up too quickly.

Tiny white bits of what once was your straw wrapper scatter on the carpet. You should really kick the habit of tearing them to shreds.

After five minutes of searching the parking lot (you tottering on your four-inch spikes), you find the car. Seat belts are buckled, the GPS is set, and your bed is in sight. That’s when you notice the gas gauge. On empty.

“Ummm, don’t you think we should stop for gas?”

He hesitates. “Well, I’m sure it’s fine. But if it makes you more comfortable…”

“It does,” you say in a voice that sounds nothing like a sweet obliging young lady on a date.

And so begins a treasure hunt, with stops at two closed gas stations, and one darkened shopping plaza that isn’t a gas station at all.

Your date shakes his head. “I think we should just head home. You can’t rely on these old GPSes.”

Right on cue, the 2011 Garmin crashes into your lap.

Miraculously, you make it all 26 miles home without breaking down. Shame you don’t plan to go out again. That would’ve made a great story. “Have a great night…” you both smile, the absent   “…see you” lingering in the air.

After releasing your squashed toes and explaining to your mom why “he’s a great guy, just… not for me. Yes, I’m positive. Yes, I’ll call the shadchan tomorrow,” you start getting ready for bed. Earrings, off. Rings, off. Necklace, off. Bracelet — hey, where is it?

You think back to the date. With no straw wrappers in the car, you played with the clasp instead… Did your bracelet fall off? Is it squished somewhere between his seat cushions, waiting to be found by whichever girl he takes out next?

You’re about to cry when the doorbell rings. Standing on the doorstep, looking as tired as you feel is… him. And sparkling in his fingers is… your bracelet.

“I noticed it when I was on the highway,” he explains. He hands it over and is off, with a grin and a wave, almost before you can stammer a “Th.. th.. thank you!”

You’re dazed. He would do that? Drive 40 extra minutes instead of texting the shadchan or something? You try to remember what bothered you on the date and come up empty. None of it seems to matter anymore. Even the crazy driving.


Stop off at 16 before falling into a dreamy sleep.


“I’m pretty tired,” you say bluntly, “can we head home?”

In the awkward ten seconds before he says, “Oh. Sure,” you see his uncomfortable realization. Oh, so she’s not having such a smashing time.

It’s a quiet walk to the parking lot.

Oh, well. Now that this date is clearly headed south, you may as well drop the dating persona and act like yourself.

“You know,” you say into the silence as he pulls onto the road, “everyone says it’s important to keep busy while you’re single. But they also say you’re supposed to come to every date fresh and focused.”

He’s listening. You exhale and continue.

“Honestly… Sometimes it’s hard to be all energetic at night after such a full day at work.”

You see something sparkle in his eyes, though he doesn’t take them off the road.

“You have a point there. So what do you do about it?”

The conversation ventures well out of official First Date territory. It generally does once guards are down, which generally happens once you decide you don’t want to go out again. Pressure’s off. Soon he’s describing the time he fell asleep on his chavrusa the morning after a date.

Feeling bold (or is it overtired?), you reciprocate with stories of your own. You’re both too involved to watch the GPS, and… miss the exit. The ETA climbs 15 minutes, but you don’t mind. Considering you don’t plan to go out again, this is your last chance to hear his controversial opinions about Ben Shapiro.

You have the answer ready before you even get home.


Continue to 15.


“You decided WHAT?” the shadchan screeches into the phone. You hold it an inch away from your ear. “You decided you’re not going out again? What kind of newfangled thought process is this? Deciding about a second date is just a formality. Everyone does it!”

“He’s a great guy, really, but I don’t want to waste his time or energy if I already know it’s not for me,” you say.

“You think you know? How could you know? Did I tell you about my nephew, the one who came home from his first date and told his mother he absolutely won’t go out again? His poor mother was beside herself. She put so much work into making the shidduch happen and then — poof — after three hours he decided it was all for nothing?

“She called me and begged me to talk some sense into her yingel. I got him on the phone and told him that he may think he knows everything, but really he knows nothing. He NEEDS to go out again. You know what? He agreed to a second date—”

“—And now they’re married with three kids?” you inject helpfully, trying to finish the story.

“No, no, when my sister called the shadchan, she said the girl didn’t want to go out a second time. But the message is still the same — you always, always need to go on a second date.”

Unless HE says no. “I’m not going to schlep a guy away from learning for another night just to delay the fact that it’s not for me.”

“Sheifeleh, for your own good, I’m setting up another date. Is seven p.m. Wednesday good?”


Since you don’t have a choice, continue to 16.


And with that, it’s settled: You and this fellow are most definitely going out again.


(Originally featured in Family First, Issue 770)

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