Questioning the “Dating Rules”

My question is about straws and how much they really say about the person you’re dating.

I am a 22-year-old bochur who just started shidduchim, and I am puzzled by the multitude of spoken and unspoken rules. It’s a davar yadua that on the first date you only bring water because it’s possible she doesn’t like Snapple, and then she’ll be thirsty and you’ll be the inconsiderate guy who didn’t make sure she had something to drink. There’s also the possibility that she doesn’t drink any sugar-laden drinks, but you certainly don’t want to be the guy who brought the Diet Snapple. So water it is, until you find out what she likes. And of course, you’d have to be a real boor to forget straws because what does it say about a girl if you think she drinks straight from a water bottle?

So my question is this: Should I be following these rules because they make some sense and make me look good? Or should I just be who I am and risk a rejection because she might come home cranky and dehydrated? All kidding aside, I’m questioning the uniformization of behavior on dates. What is its value and what are the costs of just being like everyone else? I’m a pretty independent thinker, but I also want to give myself my best shot. I’d love to hear your thoughts on this matter.

Would Rather Be Drinking a Coke

Dear Rather,

TO be me or not to be me, that is the question.

And the answer is — yes, you should be yourself. The very best version of yourself that you can be. If you are generally a thoughtful person and this is a great way to be thoughtful, go for it.

Rules are a lot like clichés. They came about for a reason. And like clichés, sometimes they apply and sometimes they don’t. Your job is to figure out how this rule originated and whether it serves you in this particular instance. If it makes sense to bring nice, neutral, can’t-go-wrong-with-it water on a first date, then bring water on the first date.

If, however, the “rule” makes no sense or completely doesn’t vibe with who you are, you are not obligated to follow it. Let’s say there is an unspoken rule that after a few serious dates it’s time to go on a “fun” date to see how you interact in casual settings. Is it, “Dave and Buster’s, here we come!”? You need to analyze which part of that resonates with you and which does not. You may see the value of seeing your date in a different context because you know that life will not be one long DMC. But you might hate bright lights and loud, dingy places. Maybe what you consider “fun” is a picnic at the local park. In that case, going to Dave and Buster’s will do nothing to help grow the relationship because it is not a representation of who you are or what you like. In that context, you will likely not be your best self. Don’t go there.