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A Chronic Dieter’s Guide to Cheating

I earned this year’s round of Super Bowl gluttony. Through a combination of Brazilian jiu-jitsu, weights, running and the keto diet, I lost 40 pounds between June and the end of January. Or just in time for two football teams to destroy each other while I stuffed my face. For the game, I went to a gathering hosted by local legends for overdoing food. Per usual, they outdid themselves — providing a metric ton of smoked chicken, from-scratch jalapeño poppers, also from-scratch queso, guac, fancy cheeses and cured meats on a board. Not to mention, an herb-y cream-cheese-topped square pizza-like thing. The kitchen counter kept filling back up with food like some Harry Potter sequence. I even found a hidden crock pot with meatballs simmering away. It went on like this for hours.

I had three full days afterward before my next weigh-in. And because I’ve figured out a very delicate tightrope walk, I still lost two pounds that week. Try not to hate me. This takes work and discipline, two things I’ve sucked at for plenty of my 37 years.

More generally, there are two kinds of people who take on restrictive diets. The first are the all-or-nothings who have to stay firm always and forever. The slightest break from pattern sends them back into a tailspin of garbage eating: whole pizzas, drive-thrus, bottomless steak fries. The second is the occasional cheater. A moth to the flame who has enough common sense to divert from the fire before being totally consumed by it.

I’m a moth. I need an occasional fix. Tell me “never again” about anything I enjoy, and I’ll have it in front of me before the phrase leaves the speaker’s lips.

In spite of this, the past nine months have been transformative. I returned to 230 pounds for the first time since 2009, down from my absolute worst of 315 and following a six-month-long struggle where I didn’t budge between 280 and 290. But I still love food. Big food. Heavy food. Rich, fattening, lip-smacking food that glistens when light hits it. A life without aged cheddar is like chopping off a leg voluntarily.

Thankfully, keto allows me meat and fat indulgences (though it’s not all meat and fat contrary to what many people say) so long as I do five important things:

  1. Ass-busting exercise for at least one full, continuous hour four days a week (if you’re not sweaty as hell, out of breath and a little sore afterward, you’re not doing it right).
  2. Eat a shit ton of vegetables.
  3. Drink an even greater shit ton of water.
  4. Skip lunch and dinner once a week.
  5. Only eat as much as my body truly wants.

This is essentially how I lost another 20 pounds since that Super Bowl party. It’s also how I can cheat without diving into a giant garbage cans of nachos. Or better put, I’m still a moth, but a sensible one who hasn’t given up all the glorious eats I love; I’ve just given up eating them all the time in favor of more meals that don’t make me feel like crap.

Some other tricks I’ve learned while attempting to balance weight loss with a diet that doesn’t rob me of all culinary joy…

Lose first, then cheat

Before the Super Bowl party, there were dozens upon dozens of days and nights when I opted not to eat pizza blanketed in pepperoni or mac ’n’ cheese. There’s no fast-track to weight loss if you don’t want to spend your remaining days in restriction and insane workout regiment hell. Even when choosing something like bariatric surgery, you don’t just go under the knife and suddenly become waif-like. Daily behavior has to change — no matter what path you take.

Get into a good rhythm first with whatever approach to losing weight works for you before straying from that method. I stayed strict on keto for about the first two months before I even considered one of my all-time loves: buttered, toasted bread. On one hand, that first cheat tasted amazing. On the other, my body gave me a big fuck you afterward — a nasty stew of heartburn, spiked heart rate, sluggishness and a sickly over-full feeling that crescendoed into a precipitous energy crash. So remember, each cheat comes with a distinct physical price.

No, you don’t need — or even want — a whole cheat day

Also remember, that was after just a single (admittedly thick) slice of buttered, toasted bread. A full-on, all-day binge of American-size, high-octane garbage is gonna make you feel a million times worse. Case in point: Before the Super Bowl neared its conclusion, I felt like hot cement had been poured down my gaping maw, rapidly hardening as it coated my insides. That feeling was more than enough incentive to get right back to my way of eating, including a gym visit the next morning.

Sure, there’s a sick delight in flipping a middle finger at “the rules,” even if you’re fucking yourself. But if cutting out certain foods makes you feel good (as I found by removing nearly all starches and sugar with keto), then a whole day of cheating is like smashing your knee with a sledgehammer just because you rolled your ankle. One or two cheat meals a week are plenty, especially if you make them count. Which brings me to my next point…

Don’t waste your cheats on shitty food

McDonald’s is fucking terrible. Spray cheese is probably nuclear waste. Hostess “cakes” will probably survive a nuclear holocaust. Yes, this might be what your dumb brain is telling you that you miss. But instead, take this chance to treat yourself. Visit that restaurant you keep hearing about. Take up the friend who’s an excellent cook on the dinner they offered. Eat something truly spectacular if you’re going to briefly screw up your progress.

Work out around the cheats

I live in Chicago, home of the most glorious, gout-inducing culinary clusterfucks ever conceived. We’re the savages responsible for deep dish pizza, but we also created the Italian combo: fatty beef with fattier sausage stuffed into it, all dipped in gravy. Worse yet, I sometimes write stories about the fine pleasure-providers in the kitchens of our restaurants and their artistry. This inevitably leads me into dalliances with irresistibly delicious food that totally fucks my program. Without carefully calculated meal planning and exercise around these flings, there’s no way I’d be where I am today. So I make sure I have a particularly intense workout before entering the food version of Caligula’s palace for a night. Similarly…

Go without food for a bit. You’ll be fine

Fasting works especially well for keto because being hungry on keto doesn’t come with the fury fueled by sugar depletion. At least that’s what it feels like for me. Growing up Jewish gives me a leg up on this because every year since adolescence, I eat no food and drink no liquids for 24 hours on Yom Kippur. Add the liquids back in, and with a little practice, fasting isn’t nearly as miserable as it sounds.

I also do a tweaked take on fasting: Once a week I skip lunch and dinner but drink as much water, LaCroix, black coffee and/or tea that I can. While it was originally to balance out cheats, I’ve found over time that I flat-out feel better after a fast. It’s a reboot. I can even train well after doing so. How I sleep after a fast and how much water I drank throughout affects my performance more than how much or little I ate the day before.

Find kind people who will give you bites of their food

Small samples of enticing, yet program-destroying treats give the best of all worlds. I get the flavor for which I’ve been pining, and I’m still on point. More importantly, I still feel good. Treat these people who allow you to steal their food very, very well. You probably annoy them. Okay, they probably find you extremely annoying. So in return, help them with housework. Carry heavy boxes for them. Better yet, take them to a meal and do not ask for any of their food.