3 Dates, 3 Looks: Makeup For Every Potentially Romantic Situation

Since I guess I'm dating again, I'm breaking down three gorgeous yet simple makeup looks for three potential dates: coffee, drinks and dinner.

Even though I love flirting with dudes, I haven’t exactly been in a dating mood lately. For one thing, I’m really busy and relationships require a lot of time. For another, my last breakup was of the Surprisingly Terrible And Long In Duration variety, and it left me a little traumatised.

OK, a lot traumatised. I’ve been on dates with dudes since, but my heart hasn’t really been in it. We’ve all been there.

But now, thanks to the healing powers of time, I’m starting to feel a little more stable and relaxed, and my heart has made a full recovery. I’m ready to start dating PROPERLY again. So if anyone sees Benedict Cumberbatch out and about, tell him to call me.

While I wait for my phone to ring, I decided to imagine three common date situations and come up with beautiful, easy-to-do makeup for each of them.

Date Scenario 1: Coffee

OK, so it’s the weekend and I’ve been talking to this person, but I’m not sure if I want to sit in the dark at a bar with them yet. Or maybe I spontaneously have a free couple of hours, and hey! Let’s meet for coffee!

The look here is going to be glowy and bright-eyed. Great for a casual date where you want to make an effort, but not look overdone.

Start by perfecting your skin a little with a lightweight BB Cream or tinted moisturiser. My BB is from Smashbox, and I like it a lot. Then cover up any spots and dark shadows under one’s eyes with concealer, and set it all with a light dusting of powder.

This will give you a beautiful, even blank canvas upon which to create further loveliness.

Lately I’ve been skipping blush in favour of highlighter only. You guys know that MAC’s Silver Dusk is one of my ultimate favourite products ever, and I’ve been really liking the look of just applying a little bit of that to the apples of my cheeks, along my cheekbones (layering it thicker in an arc around my eyes) and down the bridge my nose. It gives me a glow without adding any colour, and I’m really digging how simple and dreamy it looks.

Next, apply a light, shimmery eyeshadow across your lid and blend it upwards towards your brow, so it isn’t just SITTING there. This is the lightest colour from the Napoleon Perdis Chicago palette; kind of a slightly shiny pink-beige.

Instead of eyeliner, take a very small brush and sweep a matte brown eyeshadow underneath your lower lash line. I’m using a light brown (MAC, Wedge) because I’m fair, but find which shade works best with your colouring.

I like this trick for casual makeup, because when you’re going pretty minimal everywhere else, eyeliner can often read as too heavy and severe.

Then curl your eyelashes, fill in your brows however you like (for me, this is an angled brush and the same light brown, matte eyeshadow and I applied under my eyes) and apply mascara to top and bottom lashes. Now your eyes are done! Yay!

Finally, keep it simple but awesome with the lips. Revlon’s Balm Stains are pretty much the greatest things ever--you guys turned me on to them, and I am never going back, EVER. They’re perfect for a casual date because they’re shiny and light enough to wear during the day, but don’t be fooled, because the “stain” part of Balm Stain means that even if you eat a muffin, your lips are still gonna look gorgeous.

I’m wearing Lovesick, which is a cool deep pink that really becomes the focus of the look.

Bonus: If it’s the weekend and you don’t feel like putting your contacts in, this makeup looks mega-cute with awesome glasses!

Here is a swatch of all the colours that I used:

Now I’m ready to go forth and flirt over lattes and tea!

Date Scenario 2: Drinks in the evening-ish

My nights of going out at 9 P.M. on a Thursday for drinks are over. Now I’m way more likely to tell an aspiring boyfriend to meet me at, like, 6:30 for a drink so that if it’s fun we can spend more time together, and if it sucks I can run home and not have my entire night ruined.

Plus, it works around Oliver’s schedule. Everyone with a dog is nodding right now, like, YES SHE’S RIGHT THIS IS VERY IMPORTANT.

The problem with this time of day is that you’re going to be dealing with both sunshine AND more flattering evening light. So you need makeup that looks awesome no matter what kind of lighting situation you stumble into.

Submitted for your approval: defined cheekbones and matte lips.

I prepped my skin exactly the same way that I did before: BB Cream, concealer on spots and circles, then finish with powder. Please scroll up so you can see what that looks like.

Next I used a very light powder bronzer (MAC Mineralize Skinfinish, Soft and Gentle) to define my cheekbones and add some colour to my face. I added a tiny dab of pink blush to the apples of my cheeks, then covered it with the bronzer, just because I think it makes me look extra-pretty.

My face is done! Let’s move on to the eyes.

I started by covering my entire eye, from brow to lash line, with a super-light application of Silver Dusk (my highlighting powder). By “super-light,” I mean “Whatever was left on the brush after the last time I used it.”

Next, I took a shimmery taupe and covered my lid from lash line to crease (remember: the indentation where your eyeball meets your skull). Blend it up towards your brows a little so that you can see it when you look forward.

Instead of a liquid liner cat eye, use a dark brown shadow to define the top lash line, then wing it out just a little at the ends like a very subtle cat eye. This is more subtle than a straight liquid liner cat-eye, but still makes your eyes look extra-pretty. Make sure you blend so that the brown line is soft, not harsh.

Because the cat eye is subtle & gentle, we can’t go nuts with under-eye liner. It wouldn’t match. So I’ll clue you in to my favourite easy eyeliner secret: draw a series of small dashes under your lower lashes with a soft black eyeliner, like you’re sending a secret message in Morse Code and the only letter you know is O.

This will make your eyes look super-big and bright without looking harsh, and as you can see, it doesn’t look too Twiggy in real life. The secret is using a really soft pencil.

Then I defined my brows, curled my lashes, and applied my mascara. Now my eyes are done!

Dates make me SUPER-nervous, even if I really like the person, so I wanted the lip colour that makes me feel the most confident... and of course I picked Dragon Girl by NARS.

The internet and magazines are full of very shouty articles about how YOU SHOULDN’T WEAR RED LIPS ON A DATE because DUDES HATE RED LIPSTICK (what women-who-date-women think about red lips has apparently never been recorded), but do you know what? I don’t care. There is absolutely a valid argument to be made for dressing and presenting yourself as your most attractive self on a date, but if someone is going to write me off because I wore the wrong colour lipstick, then I probably don’t want to see them again either.

One quick costume change, and here’s my finished drinks-date look!

And here is a swatch of all the colours I used:

Date Scenario 3: Dinner

I don’t know if it’s a Chicago thing, or a dudes-I-go-out-with thing, but I feel like actual “Let’s go to dinner” dates are almost extinct. I want to bring them back. So to get that ball rolling, I am going to show you how to master the ultimate fancy date makeup: THE SMOKY EYE.

I know some of you are probably grimacing right now, like “Oh no! That’s so hard!” But I promise, it isn’t. I’m gonna break it down really simply for you.

Again, start by applying BB or foundation, concealing and setting with powder. Because we’re going to get liberal with dark eyes, dab a little extra powder right under your eyes after. This will catch any leftover eyeshadow that falls and we can sweep it away!

First, apply a slightly shimmery, almost-the-same-colour-as-your-skin eyeshadow all over your eye (this is MAC’s Shroom for me). Lid to socket, guys. Get into it.

Next, apply a base of light brown, matte eyeshadow (MAC, Wedge) up to where your eyeball meets the bone of your eye socket. You want to be able to see just a little of this colour peeking over your lid when you’re looking forward.

Grab a black pencil eyeliner and line your top lash line. It doesn’t have to be perfect yet. Don’t go all the way to the very inner corner, either--3/4 of the way along is fine.

Now, get your matte dark shadow (I’m using MAC, Carbon). Put a little bit of it on your brush and sweep it like a windshield wiper along the place where eyeball meets bone to define the crease (this will still work if you don’t have a natural crease--just use a light hand and create a little depth). Blend some on the outer corner in towards your nose, about 1/3 of the way, so that your dark shadow is darker on the very outside and fades in.

Now take a small brush and get a little more dark shadow on it. Not heaps--just enough to blend with. Blend it into the eyeliner along your top lash line, smudging it and making it look less perfect.

I always line in between my lashes along the waterline with liquid eyeliner, so that I won’t end up with that weird naked-skin space thing happening. It’s a minor thing and you don’t have to do it, but I do, so I'm putting it in the story! CAN'T BE TAMED!

Clean your brush on a towel; we’re moving on to the lower lash line now.

Get your light brown, matte shadow and sweep it under your eyes. Make sure it’s blended; this is going to make a pretty gradient effect when it’s all done.

Then take a small amount of dark shadow and run it about three-quarters of the way along your lower lash line, just like you’re applying eyeliner. Blend it well into the lighter brown. Dark shadow under the eye is unforgiving if blended badly, and you want to look sexily smudged, not dead.

You can line your whole water line with black liner if you like. I don’t, because I don’t love the look on me. Instead, I use black liquid liner again and fill in the little naked gaps between my eyelashes with short, feathery strokes. This gives a tight-lined LOOK (as well as making the smoky gradient effect even better) without making my eyes look tiny.

You’re done with the dark shadow, so brush away the loose shadow under your eyes. Don’t forget this step! You’ll look super-crazy otherwise!

Finally, we highlight. This is really simple. Connect the black shadow on the top and bottom lash lines to the innermost corner with white or light shimmery shadow. If you have an arched brow, put a small dab under the highest point of your brow, too.

Finally, define your brows, curl your lashes and apply mascara. Go for a couple coats on the lashes, because hey, we’ve come this far--go big or go home.

Hooray! You’re done with your smoky eyes!

Smoky eyes take some practice, but they’re really easy once you get used to it. Plus you can do them with literally ANY dark colour!

For the rest of the face, I kept it simple with matte, rosy cheeks and neutral lips. I started with a light dusting of my favourite pink blush (NARS, Desire) on the apples of my cheeks (those are the chubby bits when you smile).

And then instead of going full beige on the lips (as the words tells you that YOU MUST with smoky eyes), I used L’Oreal Colour Riche Aqua Caresse Lacquer Lipcolour in Pink Perseverance, because it's neutral without being totally flesh-coloured. Like Annie said, this stuff STAYS PUT, so I know my lipstick will hold up throughout a meal.

After a final outfit change, here’s the final look! I really like this one, I’m a bit sad I’m not going to dinner with a dude RIGHT NOW.

And here is a swatch showing all the colours that I used:

Before I get to your thoughts, let us first have a moment of silence for my camera, which died during the photo shoot for this article. RIP, ancient P80.

OK, loves, what are your go-to Hot Date makeup looks? Is there a way for me to be less anxious about the whole “dating” thing, or is that an intrinsic part of the experience? At least I won’t have to worry about my makeup being anything less that flawless, right?