Welcome to Dear Melissa, where I answer your questions about transitioning into or completing a Whole30, successfully sticking to your new healthy habits, and figuring out how to make this lifestyle work in the real world. Today, I’m helping all you single Whole30’ers manage a first date with grace.
Dear Melissa, Is it possible to go on a first date on the Whole30? I hadn’t given it any thought until a guy asked for my number, but now all I could think is, “I’m going to have to delay him for 18 more days or I’ll come off as a food/diet freak!” Of the thousands of people who have completed the Whole30, surely some were dating singles . . . help a girl out?! -Single in Chicago Dear Single, I love this question! First, of course you can date on the Whole30—and you should! We don’t want you turning into a Whole30 hermit, and if you’re going to turn this experience into a lifelong sustainable plan, you need some practice out there in the real world. So give him your number, and then enact my 4-step Dating on the Whole30 plan:
Step 1: The Place
Ideally you’d suggest a restaurant you know will be easy to be compatible. (Pick a steak house, your favorite salad place, or Mexican, where veggie fajitas and salsa are a safe bet.) You can frame it as, “I love XX, XX, or XX, do any of these spots work for you?” This should be an easy one, because your date will want to make you happy. If your date suggests a spot that you know will be more challenging (like a pizza place), you can just say, “I’m not super big on pizza—how about Mexican, steak, or burgers?” But remember, you can eat Whole30 basically anywhere—follow the Dining Out tips starting on page 89 of The Whole30.)
Step 2: The Talk
Have the “how you eat” conversation ahead of time, before you get to the restaurant. You can open with, “Are you vegetarian?” Or “What are some of your favorite foods?” Or “Do you drink?” Let him know how you usually eat (“Yep, I eat meat, love sushi, and I drink red wine occasionally…”) but let him know that right now you’re doing this 30-day experiment, so you’re being a little more careful with your diet than usual. That’s it. Don’t make a big deal out of it. Just mention it. You’re done. If he asks follow-up questions like, “What are you doing?” you can say, “This program called the Whole30, have you heard of it?” and then explain that you’re sticking to meat, seafood, eggs, vegetables, fruit, and healthy fats for 30 days. (You can also say, “It’s kind of like Paleo—are you familiar?”) Don’t lead with what you’re not eating. Don’t talk about how grains are really terrible for you. Don’t make it sound like it’s going to be an ordeal at the restaurant. Your attitude: it’s no big deal, you’ve got it down, dinner as usual. The end. Then change the subject.
Step 3: Do Your Homework
Research the menu ahead of time, so when you walk in, you’ll have a good idea of what you can eat. Call the restaurant if you have questions about the menu. Have. A. Plan. The more comfortable you are when you sit down and the more confidently you’ll order, the more relaxed you’ll feel and the less you’ll be worried that your date things your eating habits are weird.
Step 4: You Do You
When you get to the restaurant, just do your thing as if it’s the most natural thing in the world. “No bun or cheese, please, and can I get steamed vegetables instead of fries? And please just bring me olive oil and lemon for my salad, thanks.” Don’t make a big deal about it. At all. Just do it and continue with your date. If he offers to share dessert, just say, “I’d love to, but I’m full! You go ahead, I’ll have a cup of decaf/cup of tea.” If he asks if you want to share wine, you say, “No, thanks, I’m sticking to water tonight—but you go ahead.” Remember, this isn’t weird. It’s just what you do. If your date asks questions about your diet, keep it light (“I do this once in a while to keep my cravings in check” or “I’m doing this to see if I can figure out why I’m getting headaches”). Offer to tell him more after dinner if he’s interested in the details, and then change the subject. Remember, don’t talk about food over food. (And if he’s still interested after the fact, offer to lend him your copy of The Whole30, or brief him on the details, focusing on the benefits of the program and how you’ve seen it positive impact your life.)
The End!
Yay, first date success! (Well, food-wise, at least. I can’t say for sure he won’t spend the entire meal talking about his ex-girlfriend. Or his cat. Which would be worse?) The big picture thing to remember here: the bigger a deal you make of this, the bigger a deal it’s going to look, so just roll with it. After all, if this is generally how you eat outside of the Whole30 and this date is going to stick around, he’ll have to get used to the idea that you may eat differently than he does. Plus I guarantee your date will have some quirks with his diet too, so you won’t be the only one. (And that may be a fun topic of first-date conversation! “What are some of the weird food things you like? I love scrambling my eggs with fresh fruit. Sounds weird, but it’s strangely delicious.”) Hope this helps… now get yourself out there with confidence! Best in health, Melissa
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Remember, we aren’t answering questions about the Whole30 rules via this column (use the forum!), nor are we able to offer you specific advice about your medical issue, health condition, or body composition. 
Melissa Urban is a Certified Sports Nutritionist, and the author of the New York Times bestselling book It Starts With Food and The Whole30: The 30-Day Guide to Total Health and Food Freedom. She has been featured in the Wall Street Journal, Details, Outside, SELF, and Shape as the co-founder of the Whole30 program. Melissa and her son live in Salt Lake City, UT. Photo credit: Taylor Gage, She Thrives Blog
