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February 7, 2023

Dear Melissa: Tips for Successful Dates on Whole30 and Beyond

Melissa, a long-haired smiling woman, and text that says Dear Melissa

There are more awkward conversations to dive into on a first date than the finer points of the Whole30. But that doesn’t mean you want the conversation to turn to why you subbed out the fries for a salad or brought your own dressing—which is an excellent Whole30 power move. Dates on the Whole30 are not only doable, but can be just as smooth and successful as any time outside of your 30-day self-experiment. 

The tips that follow can help you make the most out of your dinner date conversations. They don’t guarantee an evening devoid of awkwardness. But they’ll help you set boundaries around what is or isn’t on the table for discussion.

Use “I” Statements

Feel free to share a few personal reasons for eating the way you do. Try something like, “I’m sensitive to gluten and dairy makes me break out, so I usually avoid them unless it’s really worth it.” 

This could prompt a fun “what’s worth it?” conversation, where you can share some of the fun foods you might enjoy together when your program is over. (It could also force a red flag, like if you say, “I don’t really drink–it’s never been my thing” and your date responds like that’s a problem.) 

Avoid quoting the “science” because that’s just a minefield, and don’t make blanket statements like “alcohol is poison” or “gluten is terrible for your gut,” because that just sounds judgy. 

And for the love of god, refuse to debate what’s “healthiest” by always returning to commonality: “Cool! Everyone is different, and I’m a big fan of figuring out what works for you.” 

Toss out “the Whole30”

You can also straight-up prep them for what’s to come: “I’m doing a Whole30 this month–have you heard of it? I do one every year or two, because it’s such a great reset for me.” Maybe they’ve done one too, and you can talk about your non-scale victories, favorite recipes, and how you both eat in your Food Freedom! 

Or maybe you have a good conversation about how you eat or your health goals. Or maybe they scoff at the idea of a “fad diet” without asking you any questions whatsoever and you pass on the idea of another date altogether because RED FLAG–in which case, you’re welcome.

Agree to Disagree

If you discover some factors that are deal-breakers (they’re a staunch vegan and can’t stand the sight of anyone eating meat), you can switch to casual chit-chat until it’s time to let them down gently. 

If you find you disagree about beliefs that aren’t dealbreakers (exercise methodologies, the Oxford comma, the most effective way to load a dishwasher) use the opportunity to get curious and learn more about them. You don’t have to agree on everything to agree to a first date, and discussing your differences can be a good way to judge compatibility. (But if he’s not into the Oxford comma, I’d want to know why.)

Part 2: First Dates on the Whole30

Two Steps for Planning Smooth Dates on the Whole30

If you’ve made it this far, I’m assuming your get-to-know-you went well and you’ve agreed to a first date (yay!). So let’s plan your Whole30 date so it flows smoothly, y’all have fun, and you can stay accountable to your Whole30 commitment.

Step 1: Have the conversation

Have the Whole30 conversation ahead of time, before you choose the restaurant. Conversations about food over food are awkward, so make sure you talk about your dietary preferences while making plans. While you’re talking on the phone/texting/chatting, say something like, “I’m down for dinner, but I’ll need to be a little more conscientious than usual about where I eat. I’m doing a Whole30 right now–have you heard of it?”

This opens the door to talking about your dietary preferences (and theirs), and seeing how informed and open they are to your style of eating. If they ask more about the Whole30, emphasize why you’re doing the program, the benefits you’ve experienced personally, and the foods you are eating on the program. If you know you have a sensitivity to something like gluten or dairy, feel free to mention it, so they know there’s more than just a preference at play there,  and a gluten-free menu will be something you’ll always be on the lookout for.

Now is also a great time to talk about alcohol. Try, “Also, just so you know, I’m not drinking right now. I don’t mind if you do, though,” and see what happens. If they were hoping to take you to a wine tasting or brewery, you’ll want to get this preference out up front.

In the instance your date has never heard of the Whole30, here’s how you could describe it:

  • I suspect that some things I’ve been eating are taking my energy/making my anxiety worse/giving me headaches. The Whole30 is a 30-day elimination program that can help me pinpoint the trigger. I’ve done it before, so dining out isn’t stressful–but some restaurants are easier than others, which is why I’m bringing it up.

If they have follow-up questions, give them the basics of the Whole30. Share with them all of the awesome things you get to eat on the program, give an example of a delicious meal you cooked the other night, and mention a few local restaurants that have meals you know work for you.

Step 2: Plan the date

You’ve talked about your Whole30, and prepped them that your current diet (in the short-term) looks a little different than it normally does. At this point, the perceptive person would ask for your restaurant input (bonus points). If not, however, it’s time to help direct your date’s events in a way that ensures the least awkward dinner encounter.

  • “Have you heard of Vessel Kitchen? They have a delicious menu with lots of variety, and it’s pretty low-key.” (Order from their Whole30 Approved menu.)
  • “How about Mexican?” (Chicken fajita, no tortilla, extra vegetables, guacamole, and salsa–ask if they can serve the guac with sliced cucumbers or carrot sticks instead of chips.) 
  • “Do you want to grab Chipotle and eat at the park? I’ll bring a blanket and LaCroix, you can bring some fruit and whatever else you might want.” (Whole30 Salad Bowl, boom.)
  • “Yeah, I’m totally down to meet for a drink first.” (You already told them you’re not drinking, so order something non-alcoholic, as casual as can be.)

Also, don’t feel the need to frame everything around your Whole30. If they suggest Italian, you can simply say, “Actually, Italian’s not my favorite” or “I’m not feeling Italian, how about the new bistro downtown?” If they try to bring it back to your diet (“Yeah, it would probably be hard to do no bread or pasta at an Italian place…”) you can respond, “Oh, I can find something to eat pretty much anywhere, I’m pretty self-reliant, but let’s do something else.”

Once you’ve agreed on the restaurant, do the usual—scope the menu. Think about what you want to order ahead of time, even call ahead to see how willing they’ll be to accommodate your dietary requirements. Because you’ll have a solid plan, you’ll be able to focus your time and energy on your date, and not on the specifics of what’s in the salad or whether you can order your potatoes baked instead of French fried.

BONUS: If despite your best intentions, you discover the waiter left the cheese in the salad or your burger came with a bun—don’t panic. Either eat around it or send it back politely and cheerfully. Use the extra time to get to know your date better, and pat yourself on the back for navigating a challenging moment with class and grace.

I hope this helps you navigate the tricky world of first dates. Cheers to Whole30 and first date success!


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