I don’t know if it’s because I’m a middle child or because I’m just naturally argumentative, but I was always the advocate for my brother and sister growing up. When they wanted to do something (get an ear pierced, take a trip, etc.), I’d jump right into the fray making my best case for them, having no personal interest other than supporting my sibling. Or so I like to think. In reality, I might have just enjoyed winning an argument. I still do.

If it’s possible, Matt is even worse about this. Get into a tangle with him and he’ll spend all day (and night) trying to win the argument. He never gets heated or emotional, he’s just willing to keep going until the matter is settled in his favor. Agreeing to disagree doesn’t work for him.

And this, god help us, brings us to John. He started talking early and rarely stops, and he’s got stubborn on both sides. When he started at his preschool a couple of years ago, we warned the teachers that he would negotiate with them and win. I think they thought that we were just wishy washy parents who gave in easily. It wasn’t long before they realized what they were up against. Here’s roughly how it goes, using a frootie (penny candy) as an example.

1) Good manners. John knows that I’m all about manners, so he uses please as his starting position. “Mommy, may I please have a frootie?” “John, no. It’s 7:00 in the morning, you may not have a frootie.” “Pleeeeeease?” No.

2) Compromise. We taught him what the word “compromise” means, and that may have been a mistake. He always goes to compromise right away. “Mommy, I say yes, and you say no, so that means I can have half of a frootie, right?” No.

3) Negotiation. John thinks of ‘no’ as just a jumping off point, so he lowers the bar. “Can I take a nibble of a frootie? Can I lick the frootie? Can I just hold the frootie?” No. Back when I was an amateur, I might have said yes to something like holding the frootie. Now I know better. The answer’s still no.

4) Exceptions to the rule. By now, it is clear to John that he’s going to have to work harder, so he starts creating special cases. “Mommy, my back hurts, and a frootie would make it feel better. So can I please have a frootie?” “Mommy, I’m having a really tough day today. A frootie would really help. Can I please have a frootie?” Nope.

5) Precedent. Next, he looks to use the “so and so did it so I should be able to do it to” argument. “I just saw Daddy eat a frootie. Can I have a frootie?” Nine times out of ten, Matt has done the thing that I’m trying not to let John do, and I’ll admit, I find this one tricky. It doesn’t seem fair that Matt can have a frootie and then John can’t. But I’ve learned a thing or two by now, and the answer is still no.

6) Filibuster. This is where the fun really starts. Matt calls it John’s verbal gymnastics. He wants to know why he can’t have a frootie, when he will be able to have a frootie, what’s in the frootie, whether we could all have a fruitie, what would make him able to have a frootie, how many minutes it will be until frootie time, how he’ll know when it’s frootie time, and so on. He’ll just talk about frooties in a totally reasonable yet relentless way for so long that pretty soon you’re wishing you could just give him a bag of them and change the subject. But still no.

7) Hysterics. From time to time — not too often — he’ll use a tantrum as his closing argument. After all the work he’s put into the conversation by this time, I find crying to be a bit of a cop out. It never works, but he gives it his all.

Now I’ll admit that when I’m tired, distracted, busy, or otherwise off my game, sometimes he may get the dang frootie. Or whatever it is we’re arguing about on that day. But even when I’m bringing my best and I know that the answer will always be no, he sure doesn’t make it easy. I don’t even want to think about the teenage years.