Friday, February 19, 2010

Shades Of Grey On A First Date

Just a warning: I’m a very thorough writer (in case you hadn’t noticed), so this is a long post. I hope the readers find it informative and enjoyable. So grab a drink or snack and read on, dear visitor.

After reading Bored Jewish Guy's original post (and challenge) regarding the male perspective of a first date, followed by (not) The Girl Next Door’s female viewpoint, along with Bad For Shidduchim’s call for other bloggers to participate (and their diversified posts), I’ve decided to throw my hat into the ring.

To start off, one of the reasons I think that it’s worthwhile to participate in this creative exercise, aside from the fun I derive from blogging, is because I presume my entry will be a bit different from most others out there. Particularly, since I am an out-of-towner, far from home, living in the YU dorms without a car (by choice), I don’t fit the typical sort of male dater model that most posts have written about.


My pre-date prep usually begins about an hour before I depart my dorm room, which is often two hours before the actual date start time – taking into account the subway ride into the Times Square area (more on that later). More recently, I’ve actually dated a few girls who live on the other side of The Heights, which then shifts my preparation to the hour beforehand. I shave, shower, and brush my teeth. I also utilize the time spent taking care of my oral hygiene to pick through my clothing and finalize my outfit.

I admit to having no real sense of style, so my generic dating attire includes black or (on occasion) dark navy slacks with a solid colored, long-sleeved, button-down shirt. In the fall and winter I will also pick a matching sweater, and I have a specific, medium-length black overcoat I wear in colder weather. In general, I also happen to have particular items of clothing that are set aside exclusively for dating, since everyday clothing, including Shabbos clothing, tends to get worn down with repeated use, so I sidestep that by having a belt and pair of shoes I only wear on dates. This keeps my belt buckle and shoes nice, shiny, and unscratched/un-scuffed.

I also don my nicer pair of glasses (which are otherwise worn on Shabbos/Yom Tov and at weddings and are also less beaten up), which have been variably been frameless or half-frame. I very infrequently wear contacts, despite the comments I get from family members (thanks, Mom) that I look much handsomer without glasses. So while I don’t have a first date outfit, I usually pick between two or three colors for my shirt/sweater combo.

After I’ve gotten dressed, I make sure I have my room keys, cell phone, wallet containing subway card, credit card, and around $100 in cash (just in case) and a little sticky-note that has a list of Starbucks in the general Times Square area. I have one or two that I specifically favor, but it has sometimes occurred that my first choice had no free tables or, on occasion, that the bathroom was non-operational. Hence, I make sure to know the addresses of several nearby stores to function as a fallback plan. I empathize with Bored Jewish Guy’s concern for wallet-bulge syndrome, and empty out all unnecessary receipts and change. If I am not meeting the girl in The Heights and thus going with her to and from the date, I will also bring my iPod.

Additionally, in case of inclement weather, I will bring two mini umbrellas (the good, more expensive kind with the double hinged arms which will bend and revert back instead of breaking when exposed to the winds of NY rainy days), one for me, and one to offer my date, should she need/want one.

Side Point Regarding First Date Venues and General Etiquette

Begin Rant.

Before going any further, I have to get some things off my chest. After reading the other first date posts published thus far, I am appalled to learn that guys are so haphazard with planning their activity prior to a date. It is extremely troublesome to read that other guys out there don’t inform their date where they intend to take them, thus leaving the girls stuck wondering if they should eat beforehand, or what they should eat, and what they should wear, etc. That seems utterly irresponsible and very ungentlemanly. The very idea of asking a girl when she firsts enters the car if she is hungry or not is, in my eyes, offensively insensitive! She’s nervous enough as it is (as is the guy), why forcibly induce more awkwardness?!

One of my rabbeim in Israel very strongly related in his dating shiurim that a guy should not starve the girl under any circumstance. This means one of two things:

1) If they are going out at a standard meal-time on a non-food date, then he should tell her to eat something beforehand.
2) He should be conscious enough to realize that if he has dragged her around walking for some extended period of time that she might be thirsty, or if the date has lasted a number of hours since her pre-date snack/meal, he should offer to get her something to sate her growing hunger.

In every first phone call I have ever had, aside from generic small talk, I always give my date specific information about what my plan is for the date. Sometimes due to scheduling or whatever we end up going to a restaurant instead of Starbucks since dinnertime was the most convenient timeframe for going out. I’ll tell her the exact restaurant and make sure she knows if it is milchig or fleischig, and I will offer an alternative or two just in case she isn’t such a fan of that particular establishment.

I don’t feel so qualified to comment about the driving tendencies of my fellow males, since I’ve driven on all of two dates (my first two dates in fact, back in my hometown, two years ago). I also drive like an “out-of-towner” which seems to mean I keep to the speed limit and obeying all traffic signs/lights. I will say this, however: parallel parking is one of the banes of my existence (along with window blinds) and I totally messed up my attempt to parallel park on my first date.

Nevertheless, why do guys drive like madmen!? Fine if you want to take your own life in your hands when you are out driving, but doing anything risky when you have any passengers, ESPECIALLY the woman you might end up marrying, is really irresponsible. I’ve heard quotes in the name of Rav Nebenzahl, shlita that following the proper traffic laws is an absolute chiyuv for public safety and as part of the kiyum of dina d’malchusa dina.

Regarding cab protocol: hailing a cab isn’t so difficult, even for an outlander like me. Second, it just makes perfect sense that a guy should get in the cab (and I got this from a Commentator article on dating). Aside from the uncomfortable visual trespassing opportunity many have mentioned, this writer for the Commie said it prevents the girl from having to slide across the seat, thereby rumpling or misaligning her skirt. I think that makes a lot of sense and will always make note of this point to my date, and proceed to enter first and slide across to the far side of the cab.

In summary: Why are guys SO thickheaded about these rather basic factors that cater to their date’s needs and personal comfort?! I admit to being a stickler for etiquette and protocol, but so much of the other blogger’s experiences reflect a genuine lack of concern for the well being of their date and a paucity of gentlemanly behavior.

End Rant.

Travelling to the Date.

As I mentioned, I don’t have a car in this part of the country. Maintaining an automobile in the adverse weather conditions, fearing for its safety in The Heights, dealing with the hazards of New York traffic, and the convenience of public transportation simply make it clear in my mind that having a car here is more trouble than its worth.

Most often, getting to the date involves me sitting on the subway or inter-campus shuttle by myself heading toward the Stern dormitories or somewhere recognizable, often enough Toys R Us, where we meet and proceed to Starbucks. I am almost always listening to music that is very upbeat and pop-y, which can vary from groups such as Yaakov Chesed or Judablue to a niggun sung by Shlomo Katz or even something secular (gasp) like “GO” by Inoue Joe, a current J-Pop (Japanese pop) star. Sometimes I might not be in the best mood that day due to school or whatever is going on, so my goal is to:

1) Upgrade my mood to as happy as it can be.
2) Create an overly positive mindset – I want to legitimately greet my date cheerfully without resorting to a false display of emotions, masking what I’m really thinking/feeling. I can’t stand people who live behind a façade and pretend they’re actually interested in interacting with me, so I do my very best to never present that false face to a date.

I also sometimes randomly listen to a shiur on dating to brush up on some ideas I’ve heard before but want to ensure they are on the forefront of my mind. But, more often than not, I’m listening to my music, and getting jazzed up for what I presume will be a good experience (and I’ve seldom been disappointed).

In recent months, the occurrence of the girl living on the other side of The Heights has come up slightly more frequently. This is because since my shidduch suggestions have aged with me - I prefer girls around my own age, and that means that many of them are have graduated Stern/Touro, and are attending graduate school. In these cases, I walk over/take the local shuttle to where their apartment is and we head to the subway from there. The few that live at home while attending grad school have very graciously met me in Midtown, or sometimes in The Heights, so I have never had a meet-the-parents scenario. From what I’ve heard about the uncomfortable oddities of that experience, I’m glad I’ve never had to pick a girl up from her home.

I am always ever so grateful to the girl who schleps in to meet me, but it also makes me feel guilty for making her do that (though she often says it’s no big deal and prefers to date in the city). I have yet to get far enough in a relationship with any of these living-at-home types that would require me to go visit her in the nearby city she lives in (which is often somewhere in New Jersey or Long Island).

The Meet

In the vast majority of cases, I know what the girl looks like beforehand via a picture the friend who set us up sent me, or the pictures on her YUConnects/Saw You At Sinai profile. I try to get a picture before I say yes, because I’ve had several dates that were great on paper but just not attractive (from my perspective). After reading Bad4’s post on pictures (I forget which one), whenever I am offered a picture by the shadchan, I will immediately reply with the option of me sending my own picture for the girl to view, just to be fair. So far, no one’s taken me up on that offer (most just say yes).

I don’t have an overt tactic for “checking her out,” but will casually observe her general physical form over the course of the evening. In that same vein, I don’t feel the need to not-so-discreetly check out her posterior while riding an escalator or getting in a cab.

Whether I meet the girl on the other side of The Heights or at some location in Times Square, I always start the conversation by asking how her trip in was and how her day went. The first question gets a very quick, courteous answer, and the second is perfectly neutral and a good conversation opener. I usually know a bit about her educational background/career plans, so this gives me a chance to delve a bit deeper into that. She’ll often reciprocate, knowing my own career aspirations from my profile/the shadchan and inquire about me and my educational goals as well.

I also always do my best to hold open the door for her and I’ve never had anyone refuse this civil gesture. However, some have grabbed the door handle and opened it for me when I was too mentally involved in the budding conversation and totally missed my cue. In that case, I’ll thank her and offer a quip about her taking away my gentlemanly duties, which she usually finds funny (this then often leads into a discussion about those sorts of things).

I will also ALWAYS offer to use my Metro card to pay for her ride, which the vast majority of dates have accepted without question. I swipe for her first, she goes through, and then I swipe and enter after her. A small minority have insisted she use her own card since she has an unlimited/monthly whatever card, and one or two of those girls even offered to swipe for me!

Once inside the Starbucks, I will quickly scout out any free tables and of those available (if there are more than one) point it out to her so we can quickly claim it before anyone else gets the jump on us, which has happened once or twice. After acquiring our seats, and setting down our coats (if need be) I suggest that if she doesn’t have a specific drink in mind and wants to check out the menu, that she go first and decide while I hold down the fort, after which I will go order and pay for both of us when she returns with her choice.

I am not a coffee drinker at all, so I only buy one of two things, depending on the weather and my tastes at that moment : Naked Juice or a tall (small) vanilla latte. Why a vanilla latte, you ask? It was recommended to me by my married friend from my hometown who set me up on my first date when I told her that I didn’t like coffee. It’s very mild, semi-sweet, and pretty drinkable, so I’ve ordered it numerous times since then.

I always find it a little awkward to wait in line by myself after I’ve made our order, while my date sits at our table by herself. This is especially true if our table is nowhere near the service counter and I can’t even make small talk adequately. It feels like I’ve abandoned her, only moments after we’ve officially met, and it goes against my sense of gentlemanliness. Once I’ve paid and received the drinks, I quickly hop over (not literally) to the condiment/napkin stand and grab a few napkins before heading back to the table.

The Conversation

Now the fun begins!

The first “real” conversation often picks up wherever we left off when we were chatting upon entering the Starbucks. Since the “how was your day” bit can only last so long, and because we’ve pretty much exhausted that by this point, we will shift into several “safe” topics. These subjects include: Year(s) in Israel experiences, Jewish geography/mutual friends/how we know the person(s) who set us up, Jewish music (I am a HUGE Jewish music fan, so this is always an enjoyable topic, unless she doesn’t like Jewish music), current events, YU/Stern Hock, and secular popular culture.

This can then tangent into fluffier hashkafic topics, rabbeim we both know (from YU/Stern or Israel), general bits of info about our families – such as family trips, Shabbos meals, extended family relationships. Invariably, a dating story or two is brought up, both bad and simply funny. I don’t really have that many such stories to tell, but I add to my paltry list a sampling of stories that my roommates/chevrusas have shared (leaving out all essential identifying details).

I also sometimes veer off into deeper ideas of hashkafa, or some other “serious” topic which is officially a no-no. I never just stop the conversation, but do try to not go full-force with all my hashkafic/religious nuances. I think it’s important to give the girl a general sense about who I am and what my interests/beliefs are, sort of a sampling, which she will then use as part of her evaluation regarding if I deserve a second date or not.

Small pauses in conversation are normal, but I have sometimes found that some girls aren’t really into talking so much. This has shocked me, since I always though girls were the more talkative gender (no offense meant, and the Gemara in Brachos backs me up on this anyway).

In general, I don’t try to lead the conversation or guide it one way or another. I don’t have a specific set of topics I want to cover. If there is anything on her profile that warrants further discussion, I’ll save it for a later date when I’ve learned more about her and can evaluate if any minor concerns were really warranted or not, after which I would then bring them up. I also believe that proper conversation is a supposed to be give and take. If I feel that I am asking too many questions and she’s not reciprocating, I’ll try and lead her into asking me something.

Oddly enough, I sometimes find that I am the more talkative of the two of us. When I first started dating, I felt I was a real introvert, but I have since developed my conversational skills to a much greater functional degree. As one sibling put it, I used to hardly talk at all (since I have always been more of a quiet, deep thinker than social butterfly), and now I won’t shut up. So I have to be mindful of this, and will let the shadchan know if I think I succumbed to this new talkative tendency of mine just to make sure the girl wasn’t overwhelmed by the flow of information I shared.

I also happen to talk very quickly, and have worked very hard to diminish the speed of my speech. My mind just works too quickly for my lips, and this sometimes leads to mispronunciation in my haste to tell a story or whatever. When I am more consciously aware of how fast I’m speaking, I will immediately pause for breath and switch gears into a more languid expression. The slower pace of talking sometimes makes me feel like my tongue is dancing over the words that exit my mouth, which is an interesting sensation (in a good way).

The girl will often marvel at my lack of any discernable accent or noticeable out-of-towner quirks, and I’ll assure her that I’m the anomaly in the family (for better or worse) in this area, despite having living in my hometown for the first 18 years of my life. That also leads into fun discussion about background differences, usually centering on them bemoaning the typical nature of theirs and curiously inquiring about my rather different upbringing.

Using the Bathroom

When I first started dating, I was very nervous to excuse myself to use the restroom, but I have since wizened up and realize that this isn’t a big deal at all. However, the actual departure from the table and return is still a bit awkward. There is also the problem that is more applicable for guys than girls, which is making sure my fly is properly zipped up. Thankfully, I’ve never had any embarrassing incidents, but the possibility makes me a little paranoid.

After several hours since my last bathroom use before I left my dorm, combined with the consumption of an entire Naked Juice or coffee, using the facilities inevitably becomes a necessity. My problem, which still happens every now and then, is that I become so enthralled with the conversation that I ignore the pleas of my bladder and end up realizing I should use the bathroom just as we are about to leave (and before the long subway ride back), which is awkward in its own way. If I am taking the shuttle back, I’ll usually wait until I get to the Brookdale lobby so as not to interrupt the date.

Ending the Date

When the typical pauses in conversation suddenly become grindingly painful, I know we’ve run out of things to talk about. Sometimes the girl will need to catch a certain bus or meet someone to get a ride home for Shabbos, so I’m more consciously aware of needing to end the date by a specific time. If we happen to be at a restaurant, the course of the meal generally leads toward a conclusion pretty readily (and I can only ignore the waiter’s request for me to pay the bill so many times).

I usually (but not always) pick up the subtle hints that she is getting a little tired or bored, and will ask, “So, do you think it’s time to head back?” She’ll then nod her head and express an affirmation of my suspicions. We gather our things, clear the table and throw away our trash. I’m always conflicted about what I should do with plastic bottles in these stores that don’t have recycling bins (what can I say, I’ve been brainwashed, in a good way, by YU’s Recycle-mania). In such a scenario, I’ll mention recycling to the girl, and she very often expresses a similar sentiment. If she seems aghast at the idea of me putting the bottle in my coat pocket (this only works in the winter, I’m not going to carry a bottle in my hand back in the subway, but sometimes I will carry it to Brookedale where they DO have recycling bins), I’ll just swallow my greener inclination and throw the bottle away with the rest of the refuse.

And yes, I’ve had situations where we are both likeminded in this area and we each take our empty bottles back with us. Call me crazy if you will – but this only happens every once and a while when I don’t get a vanilla latte.

After we leave, I will: A) Walk her back to her dorm and hang out in the Brookdale Lounge, listening to my iPod until the shuttle arrives B) Walk her to the bus station or C) Head back to the subway with my date and accompany her back to the entrance of her apartment building.

If I am taking her back to her apartment, we continue talking, with varying results. Sometimes conversation really picks up after the lull between the official "end" of the date and getting settled in the subway, while other times all interaction is basically dead in the water. In that case, we chat lightly, but mostly about nothing in particular, while taking advantage of the noisiness of the subway ride to create breaks instead of forcing continued dialogue.

Saying Goodnight

Saying goodnight is always awkward. I have never even thought of asking the girl for a second date then and there, because that puts her on the spot unfairly, even if I can readily tell that she liked me and will say yes. I usually thank her for accompanying me and make a reference to having enjoyed myself, after she responds in kind. I then awkwardly mention something to the effect of we’ll each get back to the shadchan and see where we go from here, which she’ll agree to in very neutral, sometimes restrained fashion (if she likes me). I wish her a final goodnight, thank her again, and she makes her exit.

The Journey Back

I’m either on the subway or shuttle listening to music of some kind (depending on my mood). I prefer the shuttle if possible, especially if it’s late, since it will drop me off right in front of my dorm building (so I don’t have to trek through the local neighborhood, and in the cold if it’s winter), is free, and far less obnoxious than taking the subway in general. I lose myself in the music, ignoring everything happening around me, and reflect on the date. I usually have a good time on a first date, but I’ll also think over the one or two rough spots that might have cropped up. If I really like her, I may end up listening to bouncy wedding songs on the way back (a bit premature, I know).

The Decision

In the vast majority of cases, I will always go on a second date. I’ve never had issues with looks that were so disturbing that I’d turn down another chance. I did want to end one shidduch after a first date (the first YUConnects shidduch) since we were simply incompatible on a number of issues, but my connector guilt-tripped me into a second date (wherein I noticed the issues didn’t change at all, and I ended it then). The one other time I wanted to end the shidduch after the first date since I couldn't identify with the girl at all, despite her great qualities, and she thought the same thing.

I’ll call the shadchan and give my post-date debriefing which consists of a short summary, a highlight of the positive points of what transpired, and what I liked about her. He/she will respond, “great, I’ll call her and see what she thought.” With the exception of one girl, they always say yes to a second date.

If I hear back from the shadchan that night that she agreed to another outing, I go to bed very pleased with the results of the evening. If it’s too late to call him/her, or they say they’ll call the girl in the morning, I’m still happy, but also a little nervous that she’s going to say no (even if that hasn’t been a widespread concern).


So there you have it, after thinking about this all week and mentioning my in-progress status on numerous other blogs’ comments, I’ve finished my version of the nitty-gritty details of Shades of Grey on a first date. I hope this has been an enlightening educational read. Comments and questions are most welcome!


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  2. Interesting read.

  3. I'm already married and I've never been on a shidduch date. so the part that struck me was your descriptions of your driving style -- believe it or not, I grew up on and learned to drive on Long Island (although I'm an out-of-towner now) and I also obey the speed limit and traffic laws.

    You sound like a great guy. Too bad I don't know so many available single girls!

  4. Wow, we really do date differently. I don't live in the city so I've never been on a subway date. I really cannot imagine doing that, it would feel so weird. I forgot to mention in my post that I go to Starbucks all the time. I LOVE starbucks, and I LOVE COFFEE. Starbucks dates sure beat a lounge date. I'm guessing from your post that you don't do lounge dates. Lounge dates are really weird. It's sort of like going to a bar which is what non-jewish daters usually do. Then again, you're not going to the BAR, you're going to a table outside the bar. I've been tempted several times to ask the bar tender for a list of wines. I'm not a drinker (pina coloda and moscato wine yum...), but it would add some action to the date.
    Thanks for the post-I definitely enjoyed!

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  6. (not) The Girl Next Door - I totally forgot to mention about riding on the subway together.

    If there are seats I always try to get us to sit together, but if there is one seat I offer it to her. I've never done a lounge date, but it just seems weird in general. People go to Starbucks to meet friends and whatnot, so it's a normal thing to do, whereas the whole lounge concept (mostly public place where semi-private conversation can occur - to avoid yichud issues, etc) is entirely contrived and feels to me as though it enhances the awkwardness of the situation.

    From what I've read on the female perspective posts - almost NONE of them enjoy lounge dates.

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  8. "despite the comments I get from family members (thanks, Mom) that I look much handsomer without glasses"- I heard the chicks dig four-eyed guys. My own glasses-wearing is optional, but I'm still not sure which way to go with that.

    I regards to girls though: I've dated a few that would look gorgeous without glasses, but just "ok" with glasses, yet still wear them on dates.

    "After I’ve gotten dressed, I make sure I have my room keys, cell phone, wallet containing subway card, credit card"- Seriously man, why in G-d's name do we need to know all this?

    "and empty out all unnecessary receipts and change"- From what I understand, it's improper to have anything in your pockets, so I usually use my suit-jacket's inner pockets (bulging is uncomely).

    "I also sometimes randomly listen to a shiur on dating"- There's an idea.

    Subway: I used to think that not coming with a car is simply not an option on dates, but it's starting to seem like in "the city" it's quite acceptable.

    "However, some have grabbed the door handle and opened it for me when I was too mentally involved in the budding conversation and totally missed my cue"- That happened to me with this one girl I dated EVERY TIME we got to a door. I kept spacing out while talking to her and forgot the door. I wasn't sure if she was being thoughtful or rebuking me for not holding the door. I wanted to say something, but...better off not going there.

  9. Bored Jewish Guy - I still don't get the whole dress up in Shabbos clothing thing. Granted, you should certainly dress up a bit and look nice, but why wear anything atypical from a slightly dressier (and certainly clean/pressed) version of what you normally wear? To me it adds all the falseness of the shidduch system. Granted, if you wear white and black with a hat everyday, that's one thing, but if you normally wear button down shirts, why not just jazz it up a little with nicer shoes, belt, etc?

    HaTzair - a lot of other guys (Bored Jewish Guy) for one, listed stuff like this. I figured why not. I had writtena lot more material of this sort, but drastically cut it down after realizing you point - that no one wants to hear anything extended about those details. One small bit was presumably tolerable and merely insightful.

    Having my wallet which just contains my driver's license, school ID, credit card, debit card, mini-bentscher/mincha/ma'ariv combo, and my metro card is quite slim as it is. I keep my keys under my wallet in one front pocket, and my cell-phone (which is pretty slim) in the other front pocket. No real bulges at all. It gets trickier when I bring the iPod and don't have a coat (as in the spring time), then the pockets might get a little bit bulgy, but not ridiculously so.

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  11. Bored Jewish Guy - I'm not attempting to critique you whatsoever, and you've made it clear that you think things through regarding your date attire.

    I just think it's something else when a certain form of "the system" mandates a specific type of dress (like suits) simply per official protocol, which people follow simple because they're told to.

    I am a big fan of people thinking for themselves, but acting in an appropriate, respectful fashion. That is why I would say jeans are a no-no on first dates, no matter how "modern" you are, unless the entire enterprise of dating is such a casual thing in general, which would still bother me on a different level (regarding a possibly lack of serious approach to dating).

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