Dating Boys, Part 1 of 2: How to be a Boy

There are two types of women who might be considered “aggressive.” Well, maybe more than two, but this isn’t about the taxonomy of the female genus. So let’s stick with a two-species model.

The first is a genuinely bossy woman. She is convinced that she knows the best way to do everything, and she is not shy about telling – or even enforcing – her opinion on others.

Then there’s an ambitious woman. She has a strong drive to achieve, and enjoys the feeling of accomplishment it gives her. But, something I’ve noticed: many of these women are nowhere near as aggressive in their personal lives, and can be quite passive when away from their job, hobby, or academic environs.

I was thinking about this because a specimen 2 type (S2T) called me up the other day rather distraught. She’d had a phone call with a guy, which was unusual in her Brooklyn-Bais Yaakov circles, but no matter.

After the introductory platitudes, the conversation went something like this:

Him: So, where are we going?

Her: I don’t know, what are the choices?

Him: I don’t know, I’m not from around here.

Her: Well what did you have in mind?

Him: Oh, I don’t know. Whatever you want.

Her: So, like… a lounge in Manhattan would be fine?

Him: Will you meet me there or do we go by train?

Her: Wait, aren’t you going to pick me up?

Him: Yes. Sure I could.

Her: So we’ll drive.

Him: I don’t have a car.

Her: What about borrowing?

Him: I don’t drive.

Her: You don’t drive?

Him: I don’t have a driver’s license.

Her: Really? Are you getting one?

Him: No. Why?

Her: Because, well. Um.

This conversation struck her as wrong on several levels. For those who don’t instinctively understand why, I’ll go into now in detail.

But first, a quick statement about the pre-date phone call. As a bais Yaakov maidel, the phone call is not mandatory in my circles. I was always very glad of that, because carrying on a telephone conversation with someone I’ve never met strikes me as rather awkward. I have trouble enough with people I know. However, I could respect a guy who wanted to call. I thought it showed confidence and an old-fashioned gentlemanliness – very much something out of the more courteous days of our parents.

Now I realize that all too often, it is directly from the days of our parents. Because sometimes what it means is that a guy is taking orders from his mother. With S2T’s guy, it was pretty obvious that this applied.

Here are his main errors:

1 – Plan the date. Plan. The. Date. You are the guy. You must come with at least one idea for the date. You want to give a girl options? Fine. You want to have backup or hear her feedback? Fine. But plan something. We are not comfortable spending your money without any idea of what your price range is. I regularly threaten that the next guy who pulls this on me is going to wind up paying for my sirloin at Prime Grill. But I never have done that. It would be like taking money from a little boy. A little boy who thinks he’s old enough to date.

So I always suggest a walk in the park. It’s cheap, it’s local, and it’s usually pleasant.

2 – Know the local customs. The average Brooklyn girl needs picking up. Car preferred. Yeah, it’s a large demand to make, but it stems from the same old-fashioned concern. Her parents want to know that she’s in good hands, and they want to see you first so they can give a description to the cops if it turns out she isn’t. If you don’t have a car, borrow. You can rent. You can hail a taxi or hire a driver.

The S2T was flummoxed because in her high-achieving world, one doesn’t tackle a task blind. One learns how to perform in the best manner possible before starting. If she were a guy, she’d get a license just for the sake of dating. Why didn’t he show her that courtesy?

S2T’s question wasn’t “Is this guy a total loser?” To her, that seemed self-evident. She wanted to know if it’s okay to call it off after the phone call. I said I always give a guy a second shot, so my advice would be to work something out with him: walk to a local restaurant or take the train somewhere. He might just be young, naïve. He might improve on acquaintance.

That’s what I tell her, but I know he won’t. Because I’ve gone out with these guys before. They are not men. They are boys. Mama’s boys. They think marriage is swapping one mother for another. They will wind up marrying a Type 1 Specimen who will wipe their noses for them in public, and they will not understand why.

If you want a woman who will respect you, respect her. Date with courtesy.

Continued in Dating Boys, Part 2 of 2: Warning Signs.


31 thoughts on “Dating Boys, Part 1 of 2: How to be a Boy

  1. Rowrr. You gonna hear it on this one, but I largely agree with you. However, I have found that many of these boys are victims of bad advice, and are salvageable. But that doesn’t mean you want to undertake that project.

  2. The other thing that strikes me as frustrating in this situation is that the girl is forced into the role of being more aggressive simply because the guy is SO passive. He doesn’t seem to have anything in mind about any part of the date, so of course the girl is going to have to be more assertive! Otherwise there won’t be a date at all.

  3. Speaking as a mom of a boy, you are SO right! The advice my husband has given our son is very much in line with what you are saying is proper dating etiquette. Sonny boy checks the weather report, has 2 umbrellas in the trunk of his car (his car, fully paid for by him, including insurance). He also checks the location, including parking. He has even on occasion gone to a place by himself, ordered a coke in the lounge, and then left the locale. He calls his predating. All important dating prep so that the young lady feels that she is with a competent, capable man, not a boy. He also offers choices, do you wanna go here, or do you wanna go there…..and later on in the dating process, will call the girl to set up the date and tell her the type of activity and how to dress. (Girls do not appreciate wearing 3 inch heels when doing mini-golf).

    In short: Get a clue, get a plan, (and a backup plan), get a life.

  4. Wow – strong post. I can’t comment whether such a person is a mama’s boy looking to swap mom for spouse – but I definitely agree with your thoughts as to planning the date and know the customs.

    However, those girls that live in Brooklyn but are longing for the niceness of the true out-of-town type guy (not LA, Chicago, Montreal, Toronto or anywhere with a large yeshivish community – but from one of those small cities with a small non-judgmental frum populations) should be a little more understanding. After all, you are looking for the OOT courteousness from your date – so be ready for his OOT behavior. Further, as you get more small town and less yeshivish, some of the guys really don’t any better. I would never have taken a girl to the Brooklyn Botanical Gardens, certainly not on a chol hamoed or Sunday – in Brooklyn, it practically is sending signals that Onlysimchas is next. Yet, many of my OOT friends cannot understand what is so bad about it – it just is not in their DNA. (To be clear an OOT guy in Lakewood or in any Yeshivish Yeshiva should know better.

  5. Um, I don’t care how OOT you are, a license is a must…personally, I found that calling before the date made the date itself easier and less awkward, and also gave the girl some warning that I’m a wacko, so she shouldn’t be shocked too much. After my first date ever, the shadchan yelled at me for the length of my per-date conversation (too long, not too short) and the next girl she set me up with, she told me that under no circumstances should the conversation be more than 10, 15 mins max (I didn’t listen ;))…that guy will probably marry a girl just like him, or find a friend who can teach him how to date, cuz that lack of preparedness is completely unacceptable.

  6. Sounds like you want to date Rebbetzin Hockstein’s son!

    All seriousness, great post. It boggles my mind when I hear some friends prepare for dates, especially as compared to others. It’s no surprise that the ones who are prepared are usually also far more mature and independent, as opposed to just doing what mommy says.

    Re: a license, I’d think that “OOT”ers are more likely to have licenses, since there’s not as sophisticated a public transit system in most cities, though I guess it depends where you’re from (DC and LA may be the exceptions). My friends who couldn’t drive were a bit exasperating to the young women they dated, but they also would go out of their way to accommodate as much as (reasonably) possible. And they had plans, and wouldn’t allow a date to ride the subway late at night if they could help it.

    I would add that the only somewhat unreasonable demand would be that a guy should get a license just to date and borrow cars for that purpose. It’s not necessarily cheap to get a license (not everyone can learn on their own), nor do most people feel comfortable borrowing cars – and certainly their friends won’t want to lend theirs in general, but specifically to a guy who never really drives to drive around NYC. I’ve lent my car a couple of times, but wasn’t thrilled about it – and I know of at least two friends who got into an accident with another friend’s car while borrowing it on a date. It’s a real headache.

  7. I agree that guys should plan the date and never call up if they don’t have a clue about where you’re going to go and how you’re going to get there. It frustrates me when guys call up and ask *me* where we should go. That is your job. Researching places to go in NYC is not that hard when you use google.

    That being said, I think we need to cut guys some slack in certain areas. You state, “Know the local customs.” However, I would argue that there are way too many different customs for so many different things, that it is not fair to expect guys to do everything in the exact way that you think is perfectly exactly how of course it always should be. People don’t have the same assumptions. I personally don’t care if the guy drives or if we take the subway or a taxi or whatever. I often listen to people venting to me about things that guys did wrong that were completely opposite of each other. For example, two girls will go on a date that is 3 hours long and one will complain that it was too short and one will complain it was too long. There is no set, clear-cut, guidelines of what is acceptable and what is not because it varies so much. I have gone on dates where we took the subway, and also been on dates where I met the guy at the location, and he did not pick me up from my house/apartment/dorm etc. And it was perfectly fine with me, though, then again, I am not in Brooklyn.

    The guy planning the date is a given, but so many other details that are different in different places.

    In terms of can she call it off after a phone call, there were a few times that I wanted to do that, but I don’t think it is polite. Though, I agree with you that if the phone is really that bad, it usually is the same in person.

  8. wow… this one had me laughing all the way through 😀 I’m probably more like mr. hockstein the predater. 🙂

  9. He may not be a momma’s boy. He may be just plain nuts.

    In my circle (which I didn’t think was so far away from yours, as a fellow former BYer) there is always the pre-date phone call. I find it very much necessary. Sure, some bozos call too late, so after waiting 4 hours for the call, I finally give up and brush my teeth – then he calls. Or he calls at 11:04, and he says on the message (that wakes me up), “Um, I guessed I missed you . . .” Right, because I’m having tea with the neighbors at the moment. But it’s a given that Potential Charming will call.

    Anywho, I don’t think even the bossy girls will marry Hapless Harry. If he can’t drive, how will he get the groceries? How will he get the kids from daycare? Whipped men need to drive if they’re going to be snapped up.

  10. Good post. I am often times shocked at how little guys think about anything other than “showing up” to a date from your comments. To me, it was always a given that I plan the date, and pick her up, and know what we are doing in advance and let her know. But maybe because I’m a BT and a little bit older than a lot of these guys that are basically overgrown high school kids…

  11. I once had a date where I was meeting the guy in Manhattan after his work day. Of course, my flight back was leaving later that night, so when I met him at the lounge with my luggage and he asked how I was getting home-I said very innocently-by plane. Little did I know, he didn’t bring a car. So I guess not all ‘brooklyn-type’ men bring cars. Suffice it to say, we had a nice subway ride home, me and all my luggage…

  12. Great post – and you emphasize points that need repeating (I’ve discussed it before a few times). Guys need to grow up and take charge before they embark on something as significant and life altering as dating and marriage.

  13. “I was always very glad of that, because carrying on a telephone conversation with someone I’ve never met strikes me as rather awkward.”

    This kind of amuses me. A phone conversation with a stranger strikes you as awkward, but going on a date to a restaurant with a stranger ISN’T awkward? I think both are rather awkward, but the phone conversation is less so. Personally, I wouldn’t want to go on a date with a guy I never even spoke to on the phone.

    “So I always suggest a walk in the park. It’s cheap, it’s local, and it’s usually pleasant.”

    What do you do during the winter? I once tried this suggestion on a chilly (but not freezing) day — the kind of day when you can have a nice walk as long as you dress properly for the weather. The suggestion was met with shock and protest, even though the guy could not come up with a better idea.

    “Her parents want to know that she’s in good hands, and they want to see you first so they can give a description to the cops if it turns out she isn’t.”

    And if you want to show the girl’s parents that she is in good hands, please drive safely as you are driving away from her house. Don’t suddenly speed off like a maniac, unless you want her parents to be worried about her safety for the next few hours until she returns home.

  14. Good post.

    Bad4, on a friday re-post scale of 1 to 5, I rate this an Arrrgh! -Guys like this drive me freakin’ crazy and I wish they’d stop giving guys like me a bad name!!!

    And bad4, you are a BY maidel? How would you describe what is a maidel?

  15. I can’t speak from personal experience, never having shidduch dated myself (or properly dated at all, for that matter. My husband and I skipped from being friends to being engaged.) but my inner feminist (which is actually buried very deeply and is relatively small) flared up when I read this.

    Why do we need the man to plan everything? Is it so outrageous for the woman to come up with some ideas and the man to come up with some ideas and then they agree on something?

    Why does the man have to pay for everything on the first date? Why not split the bill? Can you imagine how hard it must be for a guy who’s been dating a long time, perhaps even living on a non-NY income, to pay for all those first dates?

    And especially for someone living in NY, the public transportation Mecca of the US, why is it so expected that the man should have a car and a driver’s license? I could understand in Baltimore or LA, where the only people on public transportation are sketchy people, recently released from the asylum.

    I guess I’m just reading this and thinking, why is there so much pressure on the guy?!

    On the other hand, I agree that, if this is truly the expectation, then his failure to live up to it could indicate a less mature, less responsible, certainly more passive personality. My argument is more about why these expectations exist, and how is everyone meant to be aware of them?

  16. Hey you never know. Maybe he could be a future rosh yeshiva – Rav Shechter from YU also doesn’t drive

  17. I think that not driving, if you live in central parts of certain cities, is pretty reasonable. I, at least, never was bothered by someone who comes to get me followed by travel by public transit. In fact, even meeting at the location didn’t feel too uncomfortable for me. But my circle is quite different from yours.

  18. Sefardi Gal, it’s a lot harder than it seems. I’d like to see you plan 2 dates a week for a month, always having something interesting and enjoyable but not cliche

  19. MCP- he does not have to plan ALL of them, and I have planned dates, it just that we want him to show some initiative! He should at least plan the first 2..that shouldn’t be too hard! Besides, all ya’ll who live in the greater NY area..there is TONZ to do there…

  20. Miriam – someone advises these boys to be passive?

    Erachet – Exactly!

    Pre-dating strikes me as a little overboard, but being prepared never goes amiss.

    MCP – you can redo the same first date a few times running. It’s not like you need to come up with something scintillating twice a week – though in Manhattan I’m sure it could be done.

    Anon99 – I’ve been in more awkward situations than the Botanical Gardens. Like being asked in Boro Park if we were engaged. That’s just funny. Women who will mind won’t get an OOT guy. Oh well.

    Inkstained – I chat up people I’ve just met all the time. I have no trouble carrying on a conversation when I have visual feedback to go with the audio. Talking to someone I can’t see is awkward because you have no idea exactly what they mean or how they’re taking what you say.

    Also, I’ve walked in the winter. But yeah, some guys aren’t into it. Then you fall back on coffee. The way I figure it, if he turns down my free date, he can pay.

    LSD – Maidel = Bad4. Look it up in the dictionary.

    Sara – feminism is sooo 1970s. We’re looking to marry men here, and some of the symptoms of manhood are showing initiative, engagement, and responsibility. Yes, it’s pricey. But pressure? Why is it pressurizing to require him to have a destination in mind? Half of Brooklyn uses the Marriott as a destination. Yeah, it’s boring, but nobody calls those guys babies. They planned the minimum but at least they planned.

  21. I think the females here are overlooking something. All of you are wondering what’s so hard about planning a date. It is very easy to plan a date for yourself, i.e. putting yourself in the guy’s position and “wondering” what you’d like to do. You know what you like-he doesn’t. The correct approach in regards to this conversation would be to plan a date for the guy. Now does it seem just as easy?
    Another thing you may be missing is that guys, by nature, actually care a lot less than the girls do. That makes it much more difficult to choose one thing over another if you literally have no preference. And being that the guy knows that it matters(at least somewhat) to her he doesn’t want to choose something she won’t be happy with. So he asks her what she wants. Not necessarily out of immaturity, but more out of courtesy. It can actually be a sign of maturity that you aren’t picky about details.

  22. Pingback: I Concur; Bad4′s Dating Boys Warning Signs « Jewish White Guy Says

  23. MCP – the issue isn’t planning “cliche” dates. I don’t mind that; it’s understandable that the guy can’t be expected to come up with new and creative ideas for each dates. The issue is when they don’t plan, at all. That’s just lame.

  24. I have a friend in Yeshiva in Brooklyn no license, wonderful guy, out of towner, and is one of the most understanding people I know.
    Maybe he doesn’t fit the classic definition of cojones.
    Her loss

  25. Pingback: For Women Mostly « Bad for Shidduchim

  26. Okay, I really think you’re being unfair here. I sounded exactly like this guy on my first few dates, for two reasons:

    1) Nobody told me the guy had to plan the date. I’m from Manhattan and have barely ever been to Brooklyn, so I reasoned that it made no sense for me to pick the venue — since I was going to her house to pick her up, it would have to be nearby, and I didn’t know anything nearby. Even if it was in Manhattan, I had only just started dating and didn’t know what the conventional places were to go, whereas I figured she had probably gone out more and would have better ideas than I did.

    2) Nobody told me that in Brooklyn, the guy is expected to pick her up in a car. Many of my friends in Manhattan don’t have cars, and at least half of them don’t know how to drive, so I didn’t think this would be so unusual that I’d have to go out of my way to point it out.

    Neither of these is because I’m a loser, immature, or a boy. Possibly I am some of those things, but if so, it’s entirely unrelated. They’re because I had no relatives in the shidduch market, and frum guys don’t seem to talk about dating (or at least my friends don’t), so I had no sources of info. I wound up learning the hard way, namely by getting told by the girls I went out with. (And now, of course, this blog has given me endless new material to learn from — thanks for that!)

    So please, if you think the guy’s a jerk for not following some convention or other — tell him the convention. Maybe he’s a perfectly nice guy who just doesn’t know what people expect. Now I know to be ready with a couple of suggestions of things to do no matter what, and to explain up front to people from Brooklyn that I can’t drive, and to order at restaurants with an eye to giving my date an idea for my price range, and to either hold the door for my date or not depending on what my psychic powers tell me she expects (I wish . . .), and so on. But in all material respects I’m the same person I was a few months ago, just slightly less clueless.

  27. So let me get this straight, you said your friend is high-powered at work but not in her personal life, however when the guy who she dates (in her personal life) is not up to her workplace expectations of what men should be, she is frustrated? Doesn’t that sound contradictory to you? She should be looking for a guy who is more responsible, has something going in his life she could respect, rather than a pair of pants who is frum and doesn’t mind a high-powered at work girl.

    That being said, personally, I and my friends when we do offer the girls something to do on the date or choices, they never choose. Not once. I do not remember the girl ever choosing from the alternatives I gave her, other than knocking off a bad idea (such as she doesn’t know how to ice skate etc). At this point in my dating life, I rarely plan elaborate dates because she will not choose anyhow, so most of the time I show up and ask her if she has any ideas/preferences or things she doesn’t want to do. She always responds “oh nothing really, whatever you want” so we always end up in a Starbucks, B&N, or a walk on a nice day. Cheap. Easy. and no matter what she will go complain to her friends/parents/cat that she never has done anything interesting on a date. The script is always the same for both girls and guys

    On a side note to whomever commented about the guy having a car: Renting is very expensive. I did it for almost 2 years of dating because I did not have the money to buy a car at the time. Now that I own a car (paid for myself) it is not fancy, does not have a lot of horses underneath, nor is it quiet. However, it is dependable and i keep it clean and orderly.
    But for some reason. the girls I have taken out in the car have all commented how its noisy and their car (paid for by their parents) which they use to get around is so much quieter, newer, etc.

    There is pettiness on the part of both genders, however the girls complain more. The girls want someone responsible, but when he is they complain its not up to their standards. They want someone who is sensitive, but when the guy actually gives them an option to do something they want, they complain he’s not assertive. They want someone who is original on the dates, yet when given the option will choose the safer, less risky option. I’ve given up on that regard and just do my thing

  28. Harryer – It wasn’t her workplace expectation. It what she expects from a guy in real life: that he’ll be responsible and take the initiative. This is something most women want in a husband, kind of the way most men don’t want a virago.

    Nobody complains when a guy offers options. The complaint is when he doesn’t give options because he doesn’t have any ideas – not one. You don’t think that is worthy of complaint?

  29. This is an extreme example of a guy and it looks very nebech, but seriously, you think we are goyim who went to school with girls and had a 5th grade awkward dance already. You are our 5th grade awkward dance. We don’t watch romance movies. We don’t read teen vogue. We avoid thinking about talking to girls. It’s assur for our whole lives till suddenly we’re supposed to be James Bond. The whole shidduch system is retarded and hodgepodge and couldn’t be designed to be uncomfortable for guys. Girls and boys is a sheltered 1800s European environment until suddenly its 2017 America. As a Guy, Every male instinct is squashed and repressed through guilt and fear and then suddenly they throw you to the wolves. That’s you. Wolves. It’s not your fault and it’s not the boys fault. The boys are perfectly fine but all male instincts have been stunted by the religion. It either has to be the chasidish way where the girl is chosen for the boy or total Hefkerus and freedom to be aggressive men. We can’t have it both ways and expect dating to go smoothly. Girls have no idea what’s going on in a boys head. The whole idea of shidduch dating is retarded. The two ideas of shidduch plus dating are mutually exclusive paths.

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