Madonna or Whore: What to Wear on a First Date

Keri Lewis
6 min readJun 29, 2020
Image Credit: ID 32077231 © Jozef Sedmak | Dreamstime.com

For me, clothing is an expression of who I am — and people can take it or leave it. But with online dating, I find myself concerned with the dreaded “first impression.”

As humans, we carry with us sides of our personalities that advance or retreat depending on circumstance. Take any Jungian personality quiz online, and you’ll get an inkling of the shadows that make up the person you are. Are you a warrior, a wanderer, a victim, a mother? This Jungian theory has resonated with me recently. It seemed like I was making the same mistakes over and over, and I only realized why when I nailed my victim shadow to the wall to look at it.

People view me as a strong woman. It’s not just Crossfit, marathons or the Himalayan trek that give this impression. But as a woman who has walked away from a conservative Christian life, watched the love of my life spiral into psychosis, and slogged through the complex grief over his death; I’ve somehow managed to survive. Without a doubt, I have this warrior inside; but to be honest, she hasn’t been taking charge most of the time. My victim had taken control, and she felt at home in the panic caused by her bad decisions.

I’m now in a place where I recognize these shadowy selves, and I can give them their appropriate outlets. The victim likes to stay in bed, eat chips and watch Netflix. I can’t allow her to do that too much of the time, so I give her a day then kick her out of bed to go to the gym. She usually disappears as soon as I pull on spandex. The seductress had her opportunity as soon as the social distancing restrictions were lifted. She was in charge on her date with the Doctor, but I don’t necessarily want her dominating my love life. I keep working through it: recognizing the shadows that appear and allowing them safe places of expression before forcing them back into their corners.

I’m finally figuring my shit out — but wandering around the realm of online dating, I‘ve encountered another challenge: the Madonna-Whore Dichotomy (thanks, Freud).

I have it engrained in my bible-belt born brain if I dress seductively or act too forward on a first date, I’ll be seen not as the sweet person I am but as a “loose woman,” and men won’t take me seriously. I am a mother. I have four kids. I am nurturing and loving, but I am no saint. I am a woman with passions and desires I don’t want to hide anymore. Why should I?

The truth is, I like to dress sexy. There is power and magnetism in it, and after years of on-again-off-again body issues, I am finally feeling comfortable showing off my assets. There are Don Juans out there who are not at all interested in the holy mother, and I can spot them by reading their dating profiles. If all I want is a physical relationship, I have no problem leaving the Madonna at home for the night.

As I write this, the Madonna is yelling “Shame! Shame!” at me, as I walk down the street naked. This is a real battle between the “good girl” and the “bad girl.” Why do I feel the need to choose between them?

My second date with the doctor was a little boring. There was still physical attraction, and I didn’t really care about impressing him with my intellect. Yet the doctor, partly because of some off-handed comments, triggered a shadow I didn’t like, which basically made the seductress run away as fast as she could in her high heels.

But what about a man I respect, like Mr. Labrador?

Mr. Labrador has a chocolate lab like I do (hence the nickname I’m using for this post). He is a college instructor (like me) who has two daughters at home (also like me). In addition to teaching, he is a child therapist and BRINGS HIS DOG TO WORK. There are several ways into my heart, and one happens to be the way a guy treats his dog. Unbeknownst to Mr. Labrador, he already had an advantage. His messages were friendly and warm, and I wanted to make a great first impression on our date.

This created a dilemma: How should I dress? Would Mr. Labrador respect me if he’s distracted by my cleavage? A guy friend of mine who is also online dating, let’s call him Señor Salsa, told me I should always err on the side of sex appeal. So, I wore what I considered sexy: a short white skirt and a form-fitting pink top.

As I checked out my own ass in front of the full-length mirror, I wondered: Will the miniskirt clash with my master’s degree?

Mr. Labrador was waiting for me at a candlelit table for two outside the restaurant. When I said his name, his face lit up. God, I’d forgotten how nice that is! At this point, he was probably relieved my online photos were up-to-date. I’d only seen two pictures of him. In one he’s wearing sunglasses, and in the other, his face is obscured by a camera. As I’ve discovered, online dating photos are like hotel pictures: you have to add at least five years of wear to them. I was pleasantly surprised because Mr. Labrador was much more attractive in person than in the two vague photos online.

Mr. Labrador wore what I consider handsome attire: a pin-striped button-down shirt and nice slacks. He had sparkling blue eyes behind his trendy glasses and a good smile. Most importantly, he smelled good. He’s a little older than me, but he didn’t smell old like some guys do. (Seriously, men, don’t wear something your date would find in her dad’s medicine cabinet — it’s a huge turn off).

We chatted a little, and as the conversation went on, I started to feel frustrated by my German skills. So there I am, this sexy-looking woman, talking like a child who mispronounces big words. It was not the intellectual stimulation I wanted to provide. Then he tried speaking English — and it turns out, he had the same problem! We laughed about it and figured out that because we both understood the other language better than we spoke, he would speak German and I would speak English.

We ended up conversing this way for three carafes of white wine and five hours. We discussed dogs, kids, politics, Covid, the US, Germany, teaching. We basically solved all the world’s problems. We laughed and lightly touched each other’s arms while talking. When the restaurant closed up around us, he asked if he could pay for dinner, and we had a nice hug when we parted. Mr. Labrador is smart, funny, attractive, and it seemed he could look past my cleavage to find the same qualities in me.

A man who sees either the Madonna or the whore is not the guy for me (or for anyone). Likewise, I have to remind myself sexuality and intellect are not a dichotomy. We can meld them into one smart, sexually-charged package. I don’t want someone to love me purely for my body or purely for my intellect. The first option burns itself out too quickly, and the second doesn’t ignite at all.

The second date with Mr. Labrador will be the real proving ground. I will get to see more of his personality and how he acts under fire. I will find out if he has a Madonna-Whore view of women, or if he is one of those individuals who can appreciate a woman who has it all.

Now my only problem is: How do I dress sexy for dog-walking?

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Keri Lewis

Writer, adjunct professor, and cross-fitter with a lust for adventure. Life partner to a Labrador. Have my latchkey and PTSD. Proudly Gen X. But who cares?