Girl Talk: My Date Told Me To Wear More Makeup

A few months ago, I went on two dates with a guy I met on the online dating site OKCupid. We emailed and talked a bit before the first; I was looking forward to meeting him and wanted to look good. I usually date people I’m friends with first, so the blind date aspect of online dating makes me want to put forward a greater first impression.

For date one, I wore a new black and white polka dot dress that accentuates my cleavage, makes my waist look smaller than it is, and hugs my ass (in a good way) and, knowing his penchant for high heels from his profile, a pair of magenta suede ones. While they didn’t match the rest of my outfit, they’re a favorite pair of mine that I thought would add a pop of color, along with fishnet stockings. I love the way the silky dress felt against my skin and was glad I’d made the purchase, and indeed, it had become a staple of my wardrobe in the few weeks I’ve owned it. He appreciated it—and told me so within five minutes of meeting me—and I appreciated his appreciation. We went from a bar to a restaurant to another bar, where we made out for over an hour, and made plans for a second date.

Before the date, he told me he wanted me to “wear more eye makeup than you usually do” and wear a brighter red lipstick, with gloss. He said it in the context of a kinky command, and since we’d been engaging in some dirty talk, that aspect of his request wasn’t that out of place. Still, for me, it turned from a cute form of foreplay into a source of insecurity. What if I didn’t get have my makeup done to his liking—would he bail on the date? Would he be checking out all the women who wear makeup everyday, and wouldn’t dream of going out without it?

I grew up with a very hippie mom whose biggest concession to makeup is Clinique concealer, and while my grandmother sold makeup at a drugstore, her knowledge never really made its way to me. In college, I dressed in jeans and sweats, and while now I dress in a girlie way, about the only things I know how to do are swirl blush along the apple of my cheeks (except I rarely it), apply lipstick, and get manicures and pedicures. I’m 36, and can barely draw a straight line with an eyeliner pencil—not even with the liquid liners. Somehow, it always seems to go all over my eyelid and threaten to poke me in the eye. Mascara invariably winds up brushing against my glasses, and even lipstick, which I do wear most days, always feels like I should be using lip liner.

So, in order to make sure I didn’t disappoint him, I headed over to Sephora. For a $40 minimum purchase, Make Up Forever will spend 20 minutes giving you a makeup tutorial. Mostly, I just wanted to sit back and get glamourized. I didn’t ask a lot of questions, simply said that I wanted purple on my lids and a deep red lipstick, and let the man working on me do his thing. I tried not to peek too often, and was happily surprised to see that after applying two eye shadow colors, liner and mascara, my eyes popped and glittered, even behind my glasses. The lipstick made my lips stand out, and I bought a shadow, a liner, a lipstick and a gloss.

To give you an idea of this transformation (and please keep in mind these are both self-portraits), on the left is what I normally look like with just lipstick, and on the right is me after being made-up:

The makeup was a hit, but as fun as it was, I felt like I was playing dressup, and couldn’t help but feel like he was only interested in me because I’d followed his instructions. That can be hot, but a second date is too early to start dictating how I look, because then you can’t be sure what they’ll think of you when you’re just being yourself.

There are things that it’s acceptable to ask for in a committed relationship, because, well, you’re committed, you know each other well enough to accept the other person at their best and their worst. For me, part of dating someone does mean wanting to please them, not in a “they’ll break up with me if I don’t” way, but simply because making them happy makes me happy. But this guy made me feel like the way I present myself on a daily basis wasn’t good enough for him; I don’t know if that was his intended effect, but I’m pretty sure I’m way too low maintenance to ever live up to his standards.

I don’t regret having gone all out for our date, though. There’s something extremely fun, girlie and decadent about getting your makeup done. You’re being catered to, like when you get your hair or nails done. Even if you do know how to do it yourself, a professional can always add a little pizzazz to your appearance.