Welcome to Dear Melissa, where we answer your questions about transitioning into or or maintaining a healthy Whole9 life, helping you figure out how to make this lifestyle work in the real world. Today, we’re helping a woman get back into the dating scene while doing a Whole30®.

Dear Melissa, 

I’ve been Paleo for about three years now. I recently got out of a five year relationship with a guy was very on board with Paleo—he even did a Whole30 with me.  I am now back on the dating scene and am planning to do another Whole30 next month, but I’m worried as to the best way to approach this with new guys that I’m dating. 

I have told guys on dates that I eat a more Paleo-style diet and explain that it’s mostly meat and veggies. Most are fine with it.  But as I may be going out on dinner dates during my Whole30, I’m not sure the best way to approach it, as I will likely have to be “that girl” who needs to make many modifications. While I have no issues being like that when out to eat with family or friends, I hesitate to be like that on a date with someone I’m just getting to know, because I don’t want him to think of me as neurotic or that I have weird food issues. Also I’m worried that the guy might pick a place like pizza or Italian, which would make it very difficult to eat Whole30 style.  

It’s easy in our online community to feel normal about the way we eat, but the majority of people out there think it’s pretty weird (especially guys).  Any advice would be appreciated. –A., city/state withheld 

Dear A.,

The way I see it, you have three options.

Strategic Dating Approaches

One: The straight-up cray-cray. This is where you take your potential boyfriend down to the first floor of your particular house of crazy… and then show him the basement. Throw all your stuff on the table on the first date—“Milk makes me fart. I wear amber-colored glasses after 8 PM. I often smell like bumper plates. I will go apeshit if you use the words ‘artery-clogging saturated fat’.”—and if he nods, smiles, and says, “I can deal with that,” you know he’s a keeper.

Two: Keep things simple. In this scenario, you totally mirror his behavior for the first few dates, so you can get to know each other without any conflict. He offers to buy you a skinny soy latte? You could use the extra estrogen. He thinks girls who lift weights are too manly? Show him your best Prancercize steps. He thinks reading is boring? You’re practically illiterate. This keeps things simple until you decide whether he’s worth investing in—then you can start to tell him more about the real “you.”

Three: Be yourself-ish. Here, you decide which things are worth sharing now and which are not necessary to reveal during the first few dates. If your dietary preferences are really important to you, explain how you eat and why, but leave any fanaticism, judgment, or general argument about what’s “healthiest” out of the picture. If you find you disagree about beliefs that aren’t dealbreakers (exercise methodologies, politics, Japanese whaling practices), save hashing it out for when you know each other a little better. You don’t have to agree on everything to have a fun date.

Option number three is my pick, obviously. You want to give him enough information about the real you to decide whether you’re a good fit, but there’s no need to air all your laundry right out the gate. (Or say the word “fart.” Ever. That is extra dating advice for free right there.)

So what, specifically, should you do for your Whole30 date?

The Dating Plan

Have the conversation ahead of time, before you get to 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 or emailing, say something like:

I’m really into healthy eating and nutrition. I know that looks different for everyone, but for me, I generally eat more of a whole-foods (or Paleo) diet—meat, fish, eggs, lots of vegetables and fruit, and healthy fats like avocado and olive oil. I love sushi, a good steak, and Mexican food. What about you?

This opens the door to talking about your eating styles (maybe he’s vegan, and wouldn’t that be good to know up front?), and seeing how informed and open he is to your kind of diet. Remember, now is not the time for a lecture. If he proclaims to be a healthy eating guru—nothing but whole grains, soy, and low-fat dairy—you nod, smile, and say, “I like that you’re also into eating healthy.”

If he asks more about Paleo, skip the “this is why I don’t eat grains” at this time (because chances are, he does eat grains, and now you’re putting him on the defensive). Just emphasize why you choose the foods you do eat, and the benefits you’ve experienced personally.

Once you’ve had the general diet conversation, you can mention that you’re doing the Whole30. He’ll already know your general preferences, so now’s the time to mention that you’re doing a 30-day program, and you’ll likely be eating a little more simply during your date. You can explain the Whole30 in whatever way works for you. A few ideas:

I suspect that some things I’ve been eating are making me sleep worse/upsetting my stomach/giving me headaches. I’m doing a 30-day elimination diet to see if I can pinpoint the trigger. My diet right now looks pretty basic—I’ll be passing on wine and dessert this time—but I’m still enjoying what I’m eating, and I think the program will really help.

I’ve been eating too many treats lately, so I’m doing this 30-day program to help get my sugar cravings under control. I’ll be passing on wine and dessert, and if my order sounds a little complicated, don’t worry! Normally, I’m a lot more flexible with my diet. I just need this short-term reset to help me get back on track. 

I’ve set some goals at the gym (or in my sport), and I’m doing this 30-day nutrition program because I think it will help me recover better. The last time I did the program, I put 10 pounds on my deadlift! Right now my diet might look a little boring (no wine or desserts) and my order might be a little complicated, but it’s just for another few weeks. In general, I think it’s totally healthy to indulge once in a while. 

If he has follow-up questions at this point, you can give him the basics of the Whole30. Emphasize how the program might sound hard, but it’s really not with practice. Share with him all of the awesome things you get to eat on the program, and give an example of a gorgeous meal you cooked the other night.

Now, plan the date. You’ve talked about your general preference for healthy eating, and warned him your current diet (in the very short-term) is a little more restricted than usual. At this point, the perceptive gentleman might even ask for your restaurant input (bonus points), or even suggest you cook a meal together at home (extra 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.

“Since you like sushi too, there’s this great place downtown. Are you up for that?” (Order sashimi, bring your own coconut aminos, skip the rice.) 

“Let’s pick someplace easy Friday night—how about Mexican?” (Chicken fajita, no tortilla, extra vegetables, guacamole, and salsa.) 

“I’m totally down for a drink first.” (Order something delicious and non-alcoholic, as casual as can be. No big deal.) 

Also, don’t feel the need to frame everything around your diet. If he suggests Italian, you can simply say, “Actually, Italian’s not my favorite. How about the new American bistro that opened uptown?” If he tries 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, so don’t worry about that.”

Once you’ve got a restaurant picked out, do the usual—scope the menu, think about what you want to order ahead of time, even call to see how willing they’ll be to accommodate your dietary requirements.

Finally, don’t freak out. If, despite your best intentions, you discover the waiter left the cheese in the salad, the meatballs really do contain bread crumbs, or the vegetables were cooked in butter instead of olive oil—don’t bat an eyelash extension. You’ve done the best you can, and unless you have a serious allergy to something included in your meal, this situation is hardly life or death. Move on with your date, and don’t stress about it, especially not in front of him. (But feel free to vent to us on the forums later. Getting accidentally “dosed” with gluten is pretty annoying.)

I hope this helps you navigate the tricky world of first dates. (Unfortunately, I can’t help you pick an outfit from here, although I’m a big fan of skinny jeans and above-the-knee suede boots this season.) Cheers to Whole30 (and first date) success!

Best in health,

Is this good advice? Do you want to add your two cents? We welcome your input! Share your best advice for A. in comments.

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Remember, we aren’t answering technical questions via this column, nor are we able to offer you specific advice about your medical issue, health condition, or body composition.