Awkward Shidduch moments

One of the things I like about shidduch dating the most, is the awkwardness. Unlike most normal people, I kind of like those awkward silences when the only sound that can be heard is the crunching of ice or shaking of feet, those times when you say or your date something and you just don’t know how to respond. I also enjoy the first few moments when you pick them up and you are both trying to give each other the once over (checking out) but cant due to your positions in the car or train. .

Awkward Shidduch moments:

Initial Phone Call: In the yeshivish world the phone call lasts about 10 minutes and is a courtesy and logistics call. In my world the phone call can last up to 3 hours and can seem like a date. The problem with long phone calls, is that you build up this picture in your head and the long phone calls are always with girls who you end up being very unattractive.

Every time I make the first phone call, I hope for an answering machine, then they have to call me – cant explain that feeling but it’s a good one. Either way, I used to get very nervous during the first few minutes, no idea why, just did. One day that nervousness ended, but its been replaced by awkwardness, of the bad kind – because you don’t get to watch them in their moment.

The pickup: I pick up most of my dates with my car, do I go up to the door? Do I wait in the car, near the car, outside the car? There are so many thoughts, a lot of girls have been convinced that they should be embarrassed to be on a date, so they don’t want you actually knocking on their door – that’s a red flag for me by the way, it shows a lack of confidence in my mind, and its funny because the coolest girls I’ve gone on dates with have always told me to knock on their doors. I cant seem to understand the logic when it comes to their friends, let the friends speculate and do what they do.

I have also been told to wait in the car, as if I was the getaway car, which makes things even worse because you cant really check them out – a sitting down girl is no use to me, that’s why I hate those Facebook pictures with the girl sitting down in some pizza shop – they leave to much hidden.

Do I open the car door: The debate has lasted years and I always bring it up when the discussion turns to shidduch dating, but I always find it awkward to open the car door for the girl. Granted it gives her time to check you out as you run around the car, it also gives her time to check out my cracked windshield, terrible smell of bike clothing and stacks of clothing, energy bars and maps shoved into the seats behind her to give her a space – but it could be so awkward when you are leaving the car. Walking her to the car and opening the door is cool – but when you get out, do you tell her to wait, because no girl I have ever dated expected me to open the door and I could tell by their shocked looks when I did.

Fact is I always bring it up on the date itself, while its happening, I say I feel so stupid opening up car doors, and they always say its nice but not expected.

So…: I’m not one for awkward silences, but the opening conversation can sometimes be rough. I am a good opener, but if the girl is one of those dead fish one answer types I automatically start thinking about ways to shorten the date.

Lets say you take a cab: I have never taken a date into a cab, come to think of it, I haven’t actually gotten into my own cab in 15 years or so due to the high price of merely sitting on the pleather without even going anywhere, but some people do take dates into cabs and I always wondered about the awkwardness of the whole situation.

I have come in contact with many daters, who wont take a train on a date because they say its not proper, these are also the same people who rent cars, only park in parking lots (because they think looking for a spot will unnerve the girl – and they have to make more conversation and prove their parking skills all at once) and take the Battery Tunnel (Its supposedly faster but $5 more) all because that’s the “proper” thing to do on a date – hence, those two drinks cost much more than just two drinks – back to the cab ride…

If you don’t keep negiah, that’s one thing, but if you do keep negiah – that’s when the awkwardness begins. Anyone that has ever taken a cab in New York City knows that sitting in the front is generally not an option – besides, if you sit in the front and your date is in the back, that looks pretty weird doesn’t it?

So you two shomer negiah daters are in the back and suddenly you hit a sharp turn or the cabi curses at the pothole he just had to swerve to avoid and you find yourself sliding quickly across the cracked pleather in the direction of your date, what’s a yeshiva bochur to do?

Can you grab the suicide handles before you slide into your date, creating an awfully awkward situation? Or do you just let gravity take control?

Has anyone ever experienced this?

When and how to end the date: Shidduch protocol says that dates need to be at least 3 hours long, but this was before modern orthodox folks started shidduch dating. Judging by the length of shabbos davening you think the modern folks like long dates, but that’s not always the case. I like long dates when it’s a good date, and I can tell within about 5 minutes of meeting them if its going to be a good date. One time I picked up a girl in Passaic and did the thing that most Shidduch daters will never do – I took her to a restaurant in her hometown – I just couldn’t tell her right there that she wasn’t for me. I wanted to so badly.

You can use the classic I have to go in order to end the date, or you can say boy its getting pretty late – whatever you may do its always awkward. I was on a date once with “spit girl” I call her that because she asked me if we could have a spitting contest off of a bridge in central park (kind of like that scene in Titanic – but this girl could hock bigger loogies than I ever could – guess that’s what Harvard Law does to you) and this girl at an 1.5 hours in the middle of a scrabble game called it quits, and just ended the date – she also walked off on her own and said that’s how she does things, I never heard back from her thank God.

Bathroom Breaks on a date: One of the girls I went out with once – who may be reading this – told me she was quite offended when I told her I was going to go pee behind a dumpster. In my mind I rejected her right there, the next time I really needed to pee on a date, I asked the girl politely and she told me that it was nice to ask her but that she thought it was disgusting. These two girls were obviously not for me, because I like girls that prefer to pee outside and can do it anywhere at anytime. But what happens if they need to go?

My buddy was on a date once and the girl kept farting, the windows were open so she assumed he had no idea, when they got to where they were going she immediately excused herself for upwards of half an hour. Now that’s awkward, whats a girl going to say after a power dump on a date? What if it were one of those bathrooms that didn’t have a lock and he walked in on her when he needed to go? Just trying to paint embarrassing but funny situation. Of course what happens if its you that ate a predate takeout Chinese meal? The real question is whether or not to tell your date you may be awhile.

Paying: There was only one time I contested a bill on a date, most people don’t feel comfortable enough with themselves to do this and suck it up, but I thought they must have had something wrong when I was charged over $40 for a couple of games of bowling in the Five Towns, the girl saw my eyeballs bulging and told me she would pay for dinner – I accepted.

My good buddy went out the other night to walk on the highline in NYC with his date, then they went for drinks at the Carlyle Hotel, when he got the bill he tried to maintain composure, he’s the type of guy who takes cabs rather than trains on dates – the bill for 2 martinis was a whopping $84 – I was exasperated myself – he told me the drinks were $18 but, he didn’t realize it was $20 per person just to sit down – $10 if you sat on a stool – they obviously aren’t counting on the shidduch crowd. He has been calling the hotel complaining ever since, but on the date he acted cool and casual – I wouldn’t have.

I have spoken before about the half wallet pull, this is when the girl makes a gesture of paying but has no intention to pay. I wish I were in the dating scene, because I would test these girls to see if they would really pay. We do all the work, we pick them up, open doors, and chose a place – the least they could do is pay. I have let quite a few girls pay for me – some of them thought it was confidence and I told them it was really because I just don’t like buying things for people I don’t know, I love taking my friends out for dinner – but some random girl, uh uh. Most girls offer to pay, or make some sort of non-committal offer, such as the half wallet pull, the raising of the purse and the “oh let me get it” but its all fake – they want the free stuff and will be shocked if you let them pay.

Looking at the bill can be awkward too, what if they over charged you? What if you don’t have enough money? What if your just shocked like my friend was, she is studying your moves you know?

Rejection: I was sitting in a Chinese restaurant with a girl who I didn’t intend to see again, instead of waiting until I dropped her off she decided to ask me if we would be going out again. She was a tough girl, and she was obviously very into me – I said no and she asked why. I did what no man should ever do – I told her the truth – and it was because I wasn’t into her looks. Talk about awkward, her first question was “Is it because I’m fat” she wasn’t fat, a little chunky sure, but I had just taken her on a 15 mile hike and she survived just fine – it was that I just wasn’t attracted her, at all. I have been into girls that most of the you would have found ugly, but its all in the eye of the beholder.

I have a problem rejecting girls, I just cant seem to do it. There have been countless girls that I couldn’t bear to call and reject so I did the dumbest thing and just left them hanging – I feel particularly bad about one of them. I went out with her 3 times, before me she had never been out with a guy more than once, I felt honored to be that guy, but after our third date I moved to Dallas and never saw her again – I never called either, but luckily I hear she got engaged.

One time I rejected a girl over the phone before ever meeting her, I didn’t say I was but she asked when we were going to go out and I told her, I didn’t think she was for me. She demanded how I could know and I told her she seemed very serious. She seemed like the type to settle down on her parents block and make babies for the rest of her life and that didn’t suit me well, we argued about it, but I didn’t budge. That was easy – but after the date is tough.

One time a shadchan convinced me to go out with a girl again even though I didn’t want to. She demanded to know why I was asking her out again because it was obvious I didn’t want to – I told her the shadchan did the classic” she might be your bashert” which I hate.