The Pros & (Very Obnoxious) Cons Of Wearing Red Lipstick On A First Date


Like thousands upon thousands of other people, I have been wearing Ruby Woo by MAC for several years. I have worn it to parties, to school, to work, to interviews, to sets, to the gym (yes, I am one of those people who wears makeup to the gym, and I know — blah blah what’s the point blah blah). I love wearing red lipstick out, but I have always been somewhat cautious of doing so when out with somebody. You know, romantically.

Red lipstick on a first date feels weird. There are tons of great reasons why wearing a bright lip is a great thing for any social situation, including (and perhaps especially) first dates, but I am quite apprehensive. There are also lots of issues that could arise, and given how much I love my tubes of red lipstick, I have thought this over quite a bit, weighing the pros and cons repeatedly. Here, allow me to explain.

Photo: Shutterstock

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    • Not-So-Miss Kelli

      Who doesn’t carry tissue? If lipstick removal is gonna be awkward, it’ll be as awkward the hundredth time as it is the first time. I wear bright lipstick pretty much every day. “Pardon me for a moment while I remove my slutty lipstick!” is my go-to, even now that I’m married. I’m the opposite of sexy anyway so It always gets a laugh, and it just makes sense. Nobody wants fruit-punch mouth.

      I had to remove a lipstick stain from a white vintage dress yesterday (seriously, how did I get lipstick on my own boob WHILE I WAS WEARING THE DRESS?) and it wasn’t fun.

      • Samantha Escobar

        I ALWAYS GET LIPSTICK ON MY OWN BOOB. Let me know if you ever find out how the hell that happens so much, plz.

      • Karen Valdivia

        It has happened to me too, and I have prety tiny boobs. ._.

    • Eileen

      I don’t see how any of the cons are reasons not to wear red lipstick on a first date versus not at all. If you really like it, wear it; whatever.

      (also if you wear lipstick to the gym that’s eccentric; it’s only wearing eyeliner or mascara to the gym that is truly weird)

      • Janika Moravskoslezský-Carter

        Exactly I love red lipstick. Never had a problem with it on any dates whatsoever. Moral of this story is wear what you want, know what you wear.

        P.S. I totally agree I would never wear eyeliner or mascara into a gym unless you want to make fool of yourself.

      • Samantha Escobar

        I wear all sorts of makeup at the gym! I’m unsure if I’ve ever made a fool of myself, as apparently, the whole “wear what you want” thing is apparently inapplicable when working out…?

      • Janika Moravskoslezský-Carter

        If you’re going into the gym to sweat heavy what’s the point of wearing it. Unless coming straight from work to the gym etc, well OK From my recent experiences in the gym some women over do it. My statement still stands “wear what you want” some women can pull it off some can’t.

      • Samantha Escobar

        There isn’t really a point to wearing makeup besides I like how it looks, and since it’s my face wearing it, why should anybody else care where I’m wearing it to? Plus, with the advent of primer, waterproof makeup and longwear formulas, it’s actually pretty easy to keep makeup on all day, regardless of sweat.

      • Janika Moravskoslezský-Carter

        Can you explain that to some of these other women who don’t know the correct steps to applying makeup. A small application of it should do the trick but going full blown as if you are going to a special event is asking for it. As for the RED lipstick in the gym, it’s a little weird in that setting I think a light application of it will do very well.

    • Pixie

      My friend got me these weird little cotton swaps. They’ve got some kind of makeup remover inside the tube and you click the tube and they’re amazing for touch ups. They’re also impossible to explain. And, I generally go with lip stain if it’s a first date.

      • Samantha Escobar

        Oooh, I think I know what you’re talking about. I forgot those existed!

    • ArtM

      Red lipstick looks completely absurd. Don’t let other women tell you that it looks “hot”. Yes I realize that women love their makeup but to a guy it just looks cold, fake, sterile, and clownish. To a guy that is attracted to women, it is SO SAD to watch you put all kinds of colored goop on your face. Please just cut it out. ps: do you really think that we want to kiss red goop?

      • Carrie Murphy


      • Samantha Escobar

        Fortunately, I do not care what you want to kiss.

      • Janika Moravskoslezský-Carter

        Colored goop on your face- LOL!! wow really that’s a low blow. I can agree not all women look good in red lipstick. I am one of them. Yes, all men want to kiss red goop. Especially if it has a flavor to it.

      • Maria

        Well then I guess it’s a good thing I don’t wear makeup to please men.

    • ArtM

      PPS: Nothing is worse than makeup at the gym. (No, wait, perfume is worse.) Seriously, do not even THINK about wearing makeup and/or perfume to the gym. (The gym is the ONE place that women routinely look really beautiful precisely BECAUSE they don’t wear makeup!)

      As far as I can tell, you are bombarded with advertising your entire lives telling you that you need to cover your face with colored goop. They drill it into your brains. But the truth is that it looks absurd.

      Read the fable “The Emperors New Clothes”. It is, sadly, not a fable at all.

      • Samantha Escobar

        I wear makeup because I don’t really care about whether or not people think I look beautiful, as bizarre as that sounds; I just really, really like wearing makeup. It has nothing to do with how “really beautiful” people think I am or if they think I look natural. I like makeup. It’s fun. It’s colorful, and I like colors.

        If I decided to change my makeup routine when people tell me to, that would be much less pro-self than, say, looking “natural” because other people find it hotter.

        Also, “The Emperor’s New Clothes” is a fable, yes. I know what you’re saying, but it is literally a fable.

      • Janika Moravskoslezský-Carter

        Nothing is worse than makeup at the gym. (No, wait, perfume is worse.)- Read my post above and Eileen’s post if you haven’t. I’m not knocking a woman for doing what she wants but it does looks kind of tacky. Seriously who would wear perfume to the damn gym. They have guys who wear Baby Oil and cologne to the gym which is a major turn off.

      • Tempuri-san

        I’m ambivalent as to whether a woman wears makeup to the gym because, well, it’s a personal choice and none of my business. I don’t personally because my pores get super clogged when I work out heavy (which I do). A bit difficult these days since I need to transition straight from work, but I’ll usually run a cloth over my face before gettin’ hardcore.

        Perfume, on the other hand, is fcking inconsiderate. I don’t care if it’s your “thing” or if you think it makes you look/feel beautiful. It’s like smoking in the middle of a restaurant, it’s that off-putting. If it’s lingering from your day, fine, but if you’ve applied it just prior to lifting or running next to someone, you’re a jerk.

    • Rezia

      Firstly: WHAT are you talking about, being insecure about your top lip?! Having read so many of you makeup tutorials, I think you are SO pretty!

      Second: I can never find the right shade of red that also magically stays on through eating. Revlon’s matte lipstick in really red is the perfect shade but it doesn’t stay on through food. And I don’t want to look like those old ladies with the plastic-y lipstick that looks like paint. Do you have any recommendations for long lasting not paint-like lipstick that would work with yellow-y golden skin?

    • Common Sense

      Moral of the story: women are vain, insecure creatures with no common sense whatsoever. Retarded monkies who failed to evolve logically and reasonably. Yeah, yeah you don’t wear makeup to impress men, sure that’s why you wear it to make yourself present better. Such insecure little hypocrites, says one thing is right but the other isn’t. What you put on is right but the other isn’t. Wow, insecure, inferiority complex much?

    • katiechasm

      My recommendation for both this post and the top drugstore reds post is Revlon Fire & Ice. It’s a light, soft red (but not pink at all) so it looks natural with pale skin, AND it magically disappeared during a makeout session once, like it wore off completely without getting all over anyone’s face. Magical.

      • katiechasm

        I am super pale and I always end up with lipstick all over my face so these aspects are important to me.