Pretty Taught Him Ugly Lessons

By Ashley Weatherspoon

Last week, I received a private Snapchat message from a guy, well not just any guy but someone I knew… and knew well. The message read, “This song reminds me of you Ash,” and the song was Yung Bleu featuring Drake, “Your Mines Still.” The lyrics to the section he sent me went something like:

“Pretty face

Pretty tempting

But pretty taught me ugly lessons

Pretty had me giving more than I was getting

So if pretty don’t come with somethin’, well, then I dead it.”

He and I met about four years ago and instantly clicked. He was cool, successful, and fun, but he was also

24 sitting on 24 mill (if you get that Drake line, give yourself two bonus points.)

He was young, handsome, talented, and successful as fuck. So, what else does that mean? He was heavily desired, heavily entertained, and had about five to seven more years of fuckery left in him. 

Luckily, I’ve officially mastered fuck-boys and was able to separate falling for him from having a good time with him, so we had fun. A lot of fun.  Nah, ask anyone who was ever around us…. WE KNEW HOW TO HAVE FUN! We laughed to the point of tears in almost every conversation. We had nights we partied until sunrise and nights we sang at the top of our lungs and danced until our legs gave out.  He thought I was the shit, and he knew how to make me feel good. He never told me no, and if it made me feel better, he wanted to be a part of it. Also because I was older than him, he respected my experience, perspective, and intelligence.

On the flip side, there were constant reminders that I had read his “type” correctly and was doing the right thing by keeping him in the friendzone. 

There was the occasional date he would be on but lie about it as an outing with a group of friends. There was the occasional trip to Greece where he would be busy for the weekend, and then some beautiful Instagram babe would tag him in a post on social media. No matter how much I tried to provide a safe space for him to be honest about other women, he wouldn’t. He was adamant — “Ashley, you’re the one for me.” “Ashley, when will you marry me?” “Ashley, let’s have a baby.”

Sure, I liked him, but I refused to be a dummy. There was no way I would make the mistake of falling for a guy like this at this time in my life. So, instead of falling into it, I would push him away. I would tell him to stop telling me he liked me and lying to me and live his life and just be friends with me.  Honestly, it felt better to have him as a friend I could count on versus another dude lying to stay in my good graces, but by taking this approach, I also prepared myself for the inevitable. 

There would be some undeserving girl who would surely see him and figure out how to snatch him up, some woman who would put up with his shit and reap the benefits… and then boom,  as I predicted, it happened —  some beautifully stunning woman he could not resist, but also could never bring home to his mother, popped up with a baby. 

Although I had warned him 100s of times about this exact situation, just like the Yung Bleu song he sent me, he had to learn this ‘pretty’ lesson on his own. Him, being the genuine but lost, but responsible young man he was, tried to do right by her. Sure enough, in Drake’s words, “Pretty had him giving more than he would be getting. ”

No matter how prepared I was for that moment, resentment started to set in. I resented him, but I also got mad at myself, not because I didn’t end up with the ring, or baby, or relationship (I certainly wasn’t willing to lower my standards for a little extra attention, company, and a cushy bank account, and I still stand on that.) but I was mad that I actually let another man get the best of me. 

They get to sit for hours on FaceTime and stare at my beautiful face ;). They get off on my quick wit, humor, and honesty. They get all of the best parts of me without committing a single thing. They get to dump their problems in my lap. They get hours of great advice. They get….

A friend. A fucking friend. 

This past week, ‘new bae’ as we’ve been referring to him on Ask Ashley: The Podcast made it clear he only wants to be my ‘friend’ because he is still in his fuckboy stage as well. Of course, the “absolutely,” “no doubt,” “yes, let’s just be friends” side of me automatically kicked in, but the feeling didn’t stay long this time. I started to feel uneasy. I began to wonder if he deserved that from me. Now, I’m here, pen to paper, standing at the crossroads. 

Do I let another man get the best sides of me without moving past a friendship? I don’t want to be the girl full of regret, resentment, and missed opportunities because I’m understanding and happy to fall into place. I make the best of every situation and every relationship, but is that by choice or circumstance?

Am I neglecting myself? 

Am I missing out on incredible men because, by the time they come around, I’ve exhausted my energy, optimism, and funny ass jokes? 

Are my maturity and ability to compartmentalize the very things that also trap me into these situations in the first place? 

I’m tired of biting the bullet. It’s starting to feel like time to reserve my time and energy for a man willing to cock back and pull it for my love, one who’s mature enough to recognize my greatness and act accordingly.

Maybe it’s time for this pretty girl to be the one who teaches a man my own pretty lesson- this pretty girl isn’t for the friend zone. She’s for bringing home to mom, she’s for the long haul, and she’s for keeps.

Pretty Taught Him Ugly Lessons


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This Post Has One Comment

  1. I love how you are so fearless in sharing. Your writing is exceptional. As a future author myself i love it here. We gonna get more than we desire keep doing you babe!!

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