Why You Will Fall In Love With The Guy Who Won’t Check All The Boxes

Why You Will Fall In Love With The Guy Who Won’t Check All The Boxes

Today is an exciting day.

Windy City Cosmo is featured on Elite Daily, an online publication written by Millennials for Millennials to give you the voice of Generation Y.

This year, as I finish writing my book, Blow Me Away: Dating in the Windy City, I will be sharing posts with you about finding love in the city, date night stories, and book reviews focusing on love and relationships.

Being single in Chicago is awesome. Yes, if you are single right now, I think you are awesome.

I see the Valentine’s Day decor, as well, but being single is truly awesome. And being in a relationship is only great if a) you love yourself, b) you find someone good for you.

Many of us are in relationships just to be in relationships or we date to date. Honestly, meeting new people is fun and exciting, but it can also be downright uncomfortable and exhausting.

Dating Detox:

This year, I have decided to take a detox. Yes, I know we are all trying to detox in January. But I don’t mean juicing or our average cleanse.

I mean I want a detox from men.

What does this mean? A detox from men means that I’m not going to say, “yes” to every guy who asks me out. And, I won’t ask men out on a date anymore. Nope. Not going to do it.

I have already dated A LOT in the city. And this year, I have decided to add filters and other activities to my life besides dating and cocktail parties. Okay, I’ll keep the cocktail parties.

I have been reading, I have been seeking out advice, and seriously, I have too many stories about the matter.

I hope you find your Mr. Perfect. I hope you find happiness and contentment in whatever stage you are in life. Single. Married. Divorced. Dating.

One of my favorite yoga instructors, Adriene Mishler, the founder of  Yoga with Adriene, a happy and successful online yoga community that offers free yoga classes, has the mantra, “Find what feels good.”

I think that’s the key to success and happiness. It’s not about doing certain things. It’s about doing things with set intentions and goals, and stretching yourself to be happy with where you are, but striving and working towards a better future and daily growth.

It doesn’t feel good to date a jerk.

It doesn’t feel good to have one night stands.

It doesn’t feel good to hurt someone’s feelings.

It doesn’t feel good to have unrequited love.

After reading Aziz Ansari’s best selling book, “Modern Romance” and sitting down with a few Chicago bloggers to talk candidly about Chicago food and dating, I was inspired to write a post for Elite Daily about love and standards.

Below is an excerpt from the Elite Daily article published on January, 6, 2016.

Elite Daily Article Excerpt:

Why You Will Fall In Love With The Guy Who Won’t Check All The Boxes

Your life is important.

You want someone special to share your life with. But this means there are compromises to be made.

I think it’s awesome being single.

I went to a blogger dinner with nine other women in their 20s and 30s, and they dished about the single life.

Honestly, they cannot find anyone they want to factor in their vacation days and sick days for, but I personally laughed a little bit inside because I never thought that’s what it meant to factor someone else in.




There are seriously too many perks to living alone and being single.

The main one is the fact that we get to do whatever we want, whenever we want.

We can work later, we can go to events, we can buy that new dress, we can set our own budget and we can vacation where and when we want to.

Factoring someone else in and caring about someone else’s happiness is hard work.

So, yes, we have boxes that need to be checked. Yes, we would like pleasure in our love lives.

Read more of the article, “Why You Will Fall In Love With The Guy Who Won’t Check All The Boxes.”

Share Your Dating Story:

Are you recently dating someone? Share your story with me in the comments.


Amanda Whitfield
Amanda Whitfield

Amanda Whitfield is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.

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