photo above by Daniela Buvat, photos below courtesy of the advisors

How many moms does it take to get me a date?

Generally speaking, I’m clueless about guys, which makes being single and heterosexual quite a struggle. My flirting game peaked in fourth grade when Jacob White and I used to trade insults across our desks. He would mock whatever book I was reading, I would dare him to eat Post-It Notes; it was beautiful. But then our desks were separated. My dating life has been in freefall ever since.

But now I’m ready to do something about it. I’ve decided I’m going to conquer love—or at least see if I can find another boy to flirt with over Post-It Notes. Considering my track record, though, I need help. Maybe it’s a sign of my desperation, but I asked my mom for flirting advice. I mean, my existence is evidence that she could land a guy, right? I have spent most of my life ignoring my mom’s advice, so I guess it is time to try a new tactic: actually following it.

Do moms actually know best? I risked my pride (and ankles) to find out from six moms in my life. Spoiler alert: I’m still single.

dating advice brandi dye

I didn’t know I wasn’t approachable. But my mom definitely thought otherwise. “Sometimes you know how people say ‘Hi’ to you and you’re like ‘Hey.’ It’s disinterested,” she said. “But when somebody says ‘hi,’ make eye contact.”

Now, I honestly could not figure out a way to be more approachable in my daily life. I think I’m very approachable. Ridiculously approachable, just ask the creepy guys at Kum & Go gas stations. But I wanted to take my mom’s advice; so I went to a coffee shop and tried to lure someone into approaching me with my amazing eye contact. Yes, it was as awkward as it sounds.

I was the epitome of coffee shop approachable: no headphones and no laptop. I was honestly smiling at a Dickens novel like I was Meg Ryan in a ‘90s rom-com. But it’s surprisingly hard to make eye contact with strangers. And smiling at a boring book made my face hurt. Yet, there was a smidge of success: I made eye contact with a guy I’ve seen at a few parties. I smiled. He smiled and waved back, but never made eye contact again. Does that count as flirting?

dating advice brandi dye

I am not a heels pro. And I definitely made a bad call in choosing my heels for the day. I wore 4-inch wedges, which should have been both respectably tall and reasonably practical, according to fashion magazines.

I swear those shoes are made of sandpaper and cinderblocks. As soon as one part of my foot went numb, another part started to hurt, especially my ankles. Limping through my day took too much of my energy to even notice any guy—let alone notice any guy noticing me.

I went through most of the day thinking, “How? Why?” but then I got a glimpse of my a** in the bathroom mirror. Suddenly, it was clear. After that moment of enlightenment, I start planning my exits by walking in front of a targeted audience or two.

I could never be the type to casually wear heels. It just isn’t worth it. But they strangely made me feel good about myself? When I wasn’t limping, I felt as if I had my life together. Every Cosmo article says that confidence is sexy, yet there were no guys falling at my (sore) feet, even though I nearly faceplanted every other step.

dating advice brandi dye

This advice is a load of crap. My grandmother is a devout Pentecostal who wears long skirts and dresses, never pants, so her advice was not a surprise. But my grandparents have been married for 52 years; my mom is 53 years old. I can do that math. On the plus side, taking my grandmother’s advice was a breeze. I just lived my life exactly the same way I have been for the past two decades and remained totally unnoticed. Nailed it.

My paternal grandmother on the other hand…well, she has her own opinions on showing some skin.

dating advice brandi dye

Yes, Granny. They still wear miniskirts. And not only did I wear a very-mini miniskirt, I wore a pleather one. It was a kind of homage: a leather miniskirt was my grandma’s signature back in the day.

There’s a certain mental preparation that has to take place when you are about to wear a very tiny skirt. People that I would continue to see on a daily basis were going to see lots of me. I came to terms with that. But I did not mentally prepare myself for wearing a small, flowy skirt that rose to Marilyn Monroe-heights in 15-mph winds. Wisely, I wore tights because I was too lazy to shave my legs, so the view of my rear end was slightly obscured.

But my bold outfit choice, matching my bold behavior, had an impact. When a cute guy sat down next to me, all I had to do was stand up; he noticed. I couldn’t tell if it was a look of appreciation or disgust, but there were definitely eyes on the skirt-region. It didn’t go beyond that, sadly. Overall, the only real double takes and comments I got about the skirt were from people who know me and know that I normally keep my a** covered.

dating advice brandi dye

I’m hilarious, so it was not super hard to make a guy laugh. I was at a ‘90s party (rocking the pleather mini) and I saw a guy who was chilling in the corner by himself. I introduced myself and went for the comedic kill.

“Why are you hanging out in the corner by yourself? I’m just over here because I came with Beyoncé and Jay-Z over there,” I said, gesturing to my friends making out on the dance floor.

I got the laugh, then a little bit of small talk, followed by … nothing.

I refuse to be blamed for this particular failure: I was smiley as hell, I approached him first, I made him laugh, I did a shoulder nudge AND put my hand on his arm. I pulled out all the stops. Yet, he did not hold up his end of the conversation. But I appreciated Mama Rodriguez’s advice. It gave me a conversational goal beyond “Hi.” Making jokes about my status as a perma-third wheel will be my new flirting go-to.

The Result

If any moms knew best, it definitely wasn’t mine. (Sorry Ma.) Being nice and approachable just doesn’t work for me. But the days when I was feeling myself were the real wins. Somehow prancing around in a ridiculous skirt gave me a boost of confidence. You have to have a certain amount of confidence to show the world that much butt. Mama Rodriguez’s advice reminded me how hilarious I truly am. That was definitely a confidence boost.

I did spend this week thinking about guys way more than normal, but at a certain point I cared less about their opinions. I just liked feeling good about myself, which is really fortunate considering I am still single and dateless. But at least I know how good I look in a pleather mini.