Anatomy of a Family Portrait

When Mrs. Bootleg and I jumped the broom in 2002, we hired someone to shoot the obligatory wedding video. The resultant DVD was off-the-charts on the unintentional comedy scale. Ten minutes into the ceremony, I was glistening like this guy.

The DVD actually includes a "bonus features" section that plays a slideshow of That Bootleg Couple "through the years". Mrs. Bootleg's photo montage runs about three times as long as mine. As near as I can tell, my parents stopped taking pictures of me as soon as I ceased being "cute".

For the record, I'm talking about the kind of "cute" that begins when one's fresh from the womb and runs through early elementary school. Right around my eighth birthday, all photographic evidence of my adolescence comes to a screeching halt. As someone who built a lightly-read blog around self-deprecation, this hurts my heart more than you could know.

My lack of Kodak moments means that the morbidly obese, pre-teen version of me is lost to history. Ditto for my corduroy nut-hugging '80s shorts, my ill-advised high-top fade and an especially embarrassing stretch when 80% of my wardrobe was purple.

My son Jalen will not have this problem.

In his 5 ½ years on earth, he's been photographed 50 million times. If the time/date stamp on our digital camera was accurate, in the 48 hours after his birth, we took 112 pictures of the boy – most from behind the restrictive confines of the neo-natal intensive care unit. Who takes that many shots of anyone from behind the equivalent of bulletproof gas station attendant glass?

Anyways, one of the many, many unwritten rules of parenthood is that a new baby makes family portraits mandatory. And, despite my enormous forehead and sunken, emaciated face, I'm OK with this. The camera does love my mug (and, to a lesser extent, Mrs. Bootleg's and the boy's, too).

Our family portraits almost always double as our Christmas cards. For the first few years, we did the cheesy studio shot with the imitation "wintry" backdrop. Last year, however, I exercised one of my rarely-used paternal vetoes and put the kibosh on the shots from "Santa's Workshop".

We did a beach photo session last fall and this year…well, we're doing a beach session again. But, it's a different beach! In the same city. Just a little bit up the coast. But, it's a different beach. I think. Let's do this thang:

Friday, October 23: OMG, I need an outfit! Here are my problems (in no particular order) – I want to wear jeans, but I don't ever wear anything but shorts outside of work. I hadn't bought a pair of jeans in years and that was when I weighed around 190 lbs. I'm 20 lbs. lighter these days. I also need a shirt and some shoes, but I've completely lost my feel for what's cool, trendy, fashionable and/or fabulous.

I opt for a pair of jeans from the back of my closet that kinda-sorta fit, a pair of three-year-old Timberland boots that I might've worn five times total and a new long-sleeve button-down shirt. I'm reasonably confident that my ensemble could've passed for timely fashion in 2000-2001. At my age, "anywhere within the current decade" is great.

Saturday, October 24: Using her God-given powers of "all up in my business", Mrs. Bootleg sniffs out the new clothes smell coming from my closet. I tell her I bought a shirt for our pictures next Friday. She explains that she's not going to get worked up over what everyone is wearing. Then, she sees my new shirt and asks me if I'm worried my broad, vertical stripes will clash with Jalen's horizontal stripes.

Friday, October 30 – 1:30 PM: We arrive at La Jolla Shores and attempt to coordinate with the photographer via cell phone. Mrs. Bootleg – who is universally known as the LAST person you want holding a map, compass or programming a GPS – is attempting to decipher the photographer's location. We get out of the car and cross the street to meet her.

1:40 PM: After a scenic walk down the shore, we realize two things: (1) we're at the wrong beach and (2) we've got no cell phone coverage. It's about 68 degrees under a cloudless sky. We have a finite amount of time before my jeans, long-sleeve shirt and boots combo drive up my body temperature to less than photogenic levels. Even worse, the clock is ticking on "Good Jalen". His hyperactive alter ego could erupt at any minute.

1:50 PM: We find the right beach, we find the photographer. All is well.

1:55 PM: The photographer wants a few solo shots of Jalen. For whatever reason, Jalen hams it up with a series of inappropriate…baseball poses? This leads to Jalen demanding the photographer capture him pretending to hit from the right side AND the left side. "I'm a switch hitter", he insisted. Can a dad be both proud and annoyed?

2:25 PM: It's been 30 minutes. The photographer is exceedingly patient and pleasant, but Jalen's starting to crack. He takes direction and appreciates structure just fine in the classroom, but on a postcard afternoon outdoors, Jalen would rather be…a five-year-old boy.

2:45 PM: The photographer attempts to get an increasingly disinterested Jalen to pose for one last set of shots. Seizing on his competitive fire, she "races" him to a large tree. As Mrs. Bootleg cheers Jalen on, I suddenly realize how this will end. "Oh, sh*t, he's gonna slide…", I say. "J! Don't…!" Too late. Jalen executes a textbook baseball slide across the grass. Oh, excuse me…across the grass that's covered in about half an inch of standing water.

2:50 PM: With one muddy leg, Jalen makes it through the final shots, but not before Mrs. Bootleg nearly killed him. With so many witnesses present, she had to bottle up her maternal rage over the baseball slide. But, when Jalen started complaining and refused to pose…an arm was grabbed, a voice was raised, a neck vein was popping…and I wasn't involved. I'd have lost that bet.

Can't wait until next year.