While I was out in LA recently, I had a lunch meeting with a notable fashion designer. We’ll call her Tasty, I suppose because I’m hungry at the moment. NO! We’ll call her Tasty because she has great taste in fashion.

Well Tasty brought a friend along to lunch and we got to a random point in the conversation when the guest was discussing the date she was going on later that night. She was super excited, like she’s been starving for a date for eons. So she completely interrupted our business meeting to describe the dress she was going to wear. “It’s kind of like a tiger print, well not really tiger but kinda like..” Right then, Tasty stopped her in her tracks.

Tasty began ranting that prints are not for dates! She was about as passionate for fashion in this moment as Bey in the breakdown of Upgrade U. “Most men are turned off by prints, it’s too aggressive and too strong… it’s just doing too much. You’re unapproachable. Your loud ass outfit should not lead the date, let the man lead.” At first I thought to myself, wow, what a generalization. But I stayed quiet of course, speaking only when spoken to in regards to women and how they look.

The guest got defensive saying all she ever wears is prints – floral, animal, argyle. At lunch she had on a white dress with hot pink flowers and green stems and a pink cardigan. It was nice for sure, for lunch or a picnic. Yet slowly I thought to myself “yea… that wouldn’t do it for me for a first date though.”

She continued to describe what she was going to wear that night as a strapless bright yellow dress with black tiger stripes and open toe shoes with some details. Needless to say, Tasty went off. “Yea, that’s nice bumblebee! What did you have on when he first approached you? I bet it was something simple that you didn’t even think was your best outfit. If that’s how he approached you, that’s the look you want to start off with. Women dress to impress other women instead of impressing men”

I couldn’t help but nod. Tasty knew what she was talking about!! I’ve been saying this for the last ten years. Women can say that they are having a bad hair day and most of the time I have no idea what they’re talking about; their hair looks great to me. Women over accessorize sometimes when I feel like we’re just chilling. Then you start to wonder if she was expecting to do more than you’re doing on the date. Like if she’s rocking her Birkin bag but we’re bowling… But all the same, sometimes I like a risk-taking woman who tries something different with her outfit, hair, makeup. Sometimes I want her to Sarah Jessica Parker it, or Rihanna it for me one time. No one wants to date a plane Jane, or do we?

I kept quiet, thinking to myself, I don’t even want to see how this turns out. But like two women, of course, they put me on the spot, “Rondel, what do you think?!” I didn’t know what to say. I mean I totally agree that women often worry about things only another woman would notice or care about. BUT, should a woman dress to a standard for a first date, even if it’s stifling her spirit? Tasty suggested a simple black dress (or some other solid color) and plain heels, no bright lipstick and definitely no red lips. Simple can definitely be sexy. But if the woman’s personality is loud and boisterous, wouldn’t playing it low key in a simple dress and heels be misleading? And fellas, are we as simple as they make us seem?

Comment and let me know what you think! And stay tuned for part two of “Who Are You Dressing For?” where I let you know what Tasty’s guest wore on her date and how it turned out.

Update: Part 2 of Who Are You Dressing For is now live!