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Dear 20-Something Single Woman

Updated: Jun 22, 2018

Dear Twentysomething Single Woman,

I would like to humbly submit my application as your role model.

I use the word “humble” but, if you knew me, you would know that this is not a word that is oft-used to describe my personality. In fact, my writing this letter as a guest-blogger on Good Letters came about in probably the least humble way possible. A few weeks ago, Madelyne wrote a letter to our cousin Georgie, in which she “remov[ed] herself from the position of [her] role model.” Within minutes, I swooped in to offer my services; when an opportunity presents itself, you shouldn’t hesitate.

But as I sat down to write the cover letter that Georgie requested, I thought “but really, why should I be someone’s role model?” What do I really know about? How am I qualified? Is my life enviable? My housekeeper* once told me in her thick Caribbean accent that I would be “an envy amongst younger women.” This lady knows her shit, and I’m terrified of her, because everywhere she goes, she commands respect. So I’m inclined to believe what she says.

So, please allow me to introduce myself. As your potential role model. I’m Meredith, Madelyne’s older cousin. Our fathers are brothers which means I’ve known Madelyne her entire life, and she has known me almost my entire life. We’ve usually gotten along, with the exception of one very emotionally-charged game of hide and seek in which she told me that I wasn’t her cousin anymore. (Fortunately, we moved past that.)

I, too, grew up in Texas. I, too, lived in DC. I, too, love plants. I, too, have traveled the world. (Although at this point, definitely not as extensively.) In 2011, I moved to New York City.  At the ripe age of 25, I was tired of working for The Man and wanted to stretch my entrepreneurial muscles. I’ve had financial and professional successes and setbacks. But that’s neither here nor there. I am not applying to be your financial or business role-model. I know people much more qualified for that. I would like to be your dating role model. Or at least, I’d like to try.

It’s really the one subject that I know the most about. In fact, if I put as much effort into building my side business as I have into dating, I would probably be making six-figures outside of my day job**. (Which is a little discouraging when put like that; I hope that doesn’t disqualify me.) But I really do know a lot, and I think that if I’m you’re dating role-model, it will help me too—to make better, smarter decisions that demonstrate that I am a woman of high value. Just like you.

Do you know the most important asset for an entrepreneur? A strong self-image. A sense of your own worth—the knowledge that you are deserving, and that alone, you are enough. I didn’t develop that type of self-image until I was in my 30s, I didn’t understand that I was enough until, like, a month ago. If we had talked before then, I would have said that, when it came to dating, I was goal-oriented. I saw dating like a competition and, to win, I needed that the perfect relationship to complement my idea of an Insta-perfect life.

But I let my longing and my desire to win overcome my judgement, and I lost my voice. I held back too much. I mentally flagged things in my mind to “circle back to,” but never circled back. I created excuses for disrespectful words and actions, and put up with bad behavior. And when I say bad behavior, I don’t mean he took a few hours to text back. I mean awful, hurtful behavior, like being stood up, lying about a relationship status, and sending unsolicited NSFW photos.

What that type of bad behavior communicates is that you are not worthy of decency. And as your potential role model, I need for you to know that you are fucking worthy. The problem is that if you’re unsure of that, my telling you won’t make a bit of difference. You have to have that moment where you finally recognize it. My moment came in the middle of a business and personal development conference for entrepreneurs.

I spent the weekend listening to speaker after speaker share inspirational stories about how they achieved financial freedom, and they all had one thing in common: they weren’t willing to settle or accept excuses from themselves. I realized that these same standards could be applied to dating. If I couldn’t accept excuses from myself, then why would I accept or chase after someone who treated me disrespectfully just because I liked him? Accepting disrespectful treatment is like shitting on everything you’ve achieved and all of the people that supported you and your goals.

That hit me like a ton of bricks, and I hope that it will hit you that hard too when you have your moment, whatever or wherever it is. Knowing that you can and will leave someone behind if they treat you disrespectfully brings you this peace about your future, it allows you to command respect. So do anything and everything you need to do to have that moment. Take a solo road trip, chase a waterfall, go to therapy, join kickboxing, get ripped, read self-development books–because the moment doesn’t come out of nowhere. You have to work for it.

And then you have to resolve. Resolve to stop holding back. If a man says or does something that raises a red flag, address it. Immediately. I’m not saying to go in guns blazing, because we’re all just here to have a good time, but if something doesn’t seem right, stand up for yourself. Show some sass. Ask questions. Call them out if you need to—it doesn’t matter if it’s the first date or the twenty-first. And don’t worry about his reaction—it won’t really matter in the end. In the end, what will matter is that you showed your backbone. (It will be way more fun!)

I look forward to your consideration for the position of role model. References are available upon request.

Warm Regards,


*She comes once a month, calm down. It’s not like I’m some baller.

**I definitely don’t make six-figures at my day job.


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