I had a date. He was very dishy, foreign, and tall, all the things I like. Plus, he was my first official date after my divorce.

I felt nervous about everything women get nervous about on first dates: that I was too thin and flat chested. Plus, my eyes looked sunken and tired, so I wanted the focus to be on my lipstick and not on my dark circles.

I had decided on a lovely raspberry lip color, but as I went to apply it in the women’s bathroom at the restaurant before meeting him, I realized I had forgotten my lipliner.

In my nervous state, I applied several coats of lipstick just in case I licked it off before meeting him, as I am a perpetual lip-chewer especially when nervous.

As I shuffled around our meeting location trying to find him, I managed to catch a glimpse of myself in a window. In the five minutes it took to go from the bathroom to the meeting place, my lipstick had grievously slipped from my lip-line to bleed around my lips.

I looked like a batty middle-aged woman. Letting out a yelp, I headed back to the bathroom for repairs. Lipliner becomes of greater importance as our lip line softens and we go on dates with dishy foreign men.

In order to protect you from a hazardous first date, here are my tips on using lipliner.

Should Your Lipliner Color Match Your Lipstick?

As an artist, I naturally gravitate away from anything that’s too matchy-matchy, like lipliner and lipstick. I’m always looking for a more creative way to highlight shape whether it be in wardrobe or makeup.

Having said that, matching lipstick and lipliner can be a good thing, depending on what you’d like to achieve. Do you want your lips to look bigger? If this is the case, then try a liner about a shade darker or more intense than your lipstick. The tricky part with going this route is blending.

I recommend applying the lipstick first in this case, and then lining on top of the lipstick. You can also line slightly over the natural lip line, but be cautious. It’s very easy to look batty if you overdraw your lips.

If your liner tends to bleed, then put foundation and powder on your lips before lipstick and this will help hold it in place.

Lip plumping products have become popular in recent years and can help make the lips look bigger and fuller. If this interests you, try Too Faced Cosmetics Lip Injection Extreme or Buxom Pillowpout Creamy Plumping Lip Powder. Besides the long crazy titles, they can help lips look fuller or be a wonderful conversation piece over tea.

Do you want to make your lips look smaller? To reduce the size of your lips, try using a non-glossy lipstick as gloss tends to attract more attention. Also, use a shade that is closer to your skin color and match your liner to the lipstick.

I have fairly full lips; therefore, I tend to apply lipstick and a closely matching lipliner, in that order. I like the easier blending of applying lipliner second, but some prefer it the other way around. Do what works best for you.

How to Line Your Lips in 4 Easy Steps

Lining your lips can be tricky, especially if your natural lip line has become softer and less obvious. Here is my step by step lip-liner technique:

Step #1: Start at the Bow

Start at the bow of your lips and find the downward arrow in the middle of the top lip. If it helps, stretch your lips so that they are thinner and easier to navigate.

Step #2: Find the Lower Middle Point

Now find the middle of the bottom lower lip line and draw in a small section so that it’s even with the top bow.

Step #3: Connect the Top

Starting from the top of the bow, connect it to the end of your top lip. Then do the same for the other side. Check to be sure that they are even.

Step #4: Connect the Bottom

Now connect the bottom line to the corner of your mouth. It should all look balanced and even. Apply lipstick as needed.

Final Lipliner Advice

Lastly, a wonderful trick to not only keep your lipstick in place but keep it on longer, is to fill in your lips entirely with liner and then add lipstick. If you do this, be careful that the liner isn’t too dark, as it will darken your lipstick shade substantially.

This technique works best when using a matching color or a neutral shade like Spice Lipliner by Mac. To be honest, Spice Lipliner is my favorite color liner, and I use it with nearly every shade of lipstick I own. It blends in well with whatever color I am wearing and doesn’t alter the lipstick shade to a noticeable degree.

Dates with tall foreign men can be dicey; don’t let your lipliner be as well! By the way, we dated for some time and still keep in touch as friends. It’s a good thing I didn’t look batty.

Do you wear lipliner? How do you apply it? Do you have a lipliner story you’d like to share? Which is your favorite lipliner color? Let’s have a conversation!