Date night makeup: How many dates should you wait to go all natural?

Scenario time. The first date: You’re all dolled up with the silky hair, bandage dress, killer heels and perfectly-done makeup. You look amazing and you know it. He knows it too. And he also knows that you’re funny and smart and charming, so he asks you on a second date. And then a third. And then you run out of sexy bandage dresses. And you’re sick of straightening your hair. And you can only get your makeup done for free at the Mac counter so many times before they catch on. So you’re wondering, how many dates should you wait to go all natural?

Any woman who’s been on a third date has been there. And the answer to that question is it depends on what’s all natural for you. So here’s a sliding scale of when you should go all natural.


You should never go all natural for him if your natural state is pretty unnatural. I’ll admit it, I wear makeup most of the time. I’ve even fallen asleep in my makeup. I’m pretty sure every beauty expert would tell you never to do that. But I’m a relationship expert. So what can you do? I say do what makes you feel beautiful. If it’s all makeup, all the time, then keep it up with your man.

5-10 Dates

You’re a gal who wears makeup when she has evening plans, and you wear a bit to work. You probably don’t wear makeup during weekend days, when you’re running errands and heading to the gym. This level of makeup wearer and comfort being all natural leaves a little more wiggle room. I say keep your makeup on when you’d normally have it on and off when you’d normally have it off. You won’t be running errands with him until you get a little deeper into dating, somewhere between five and ten dates. With that being said, you’re not cheating yourself if you wear extra makeup the first time you run errands with him, and you won’t scare him off if you don’t. This decision is all about your comfort level.

2-5 Dates

You never wear makeup, aside from first dates. Woman, three cheers for you. I say rock the bare face as soon as you feel comfortable. If you just slapped on powder for date one and are normally completely fresh-faced, go for the all-natural look as early as your second date. This is about being you and feeling great. Going from a little mascara to none is something most guys won’t even notice, and you’ll feel more authentically like yourself.

All of that being said, every guy appreciates a little effort now and then. Even though he doesn’t know how much of a pain Spanx are or what skill level liquid liner takes, every guy wants to feel like he’s on a first date with the girl he loves every once in a while. So even if you’ve gone all natural, it doesn’t mean you can’t go back every once in a while.