Dating Then & Now – Bree


I’ve been tall for a long time. Standing proudly at 6’4” for a good 20 years now.

High school is when I started noticing boys. My girlfriends would be asked out for dates or for the prom. Some of them even had steady boyfriends. That was not my high school experience.

I was always around boys a lot, because I was their friend. There was this one boy in high school. I’ll never forget him because he was a great friend, but also the boy I had the biggest crush on. He was kind, cute, and overall just a great person. He was the boy I could talk to about anything; he was always there to listen and support.

Him and the other boys at school would say, “Bree is awesome! She’s a guys girl,” but never would they say, “Bree is great! I’m going to ask her out on a date.”

Things started to shift when I went to college. I had the full college experience! I joined a sorority, did my share of partying, and made lifelong friends. College was amazing. There was some dating and I kissed a lot of frogs. My exploration of the male race was in full swing.


Three years ago I moved back to New York single and slightly bruised from trying to navigate the brutal dating landscape in Los Angeles. Sheesh, that was tough.

I settled in Harlem and that is where the love affair with the city, my neighborhood, and the people started. I found myself being surrounded by more likeminded people. Those with careers, ambition, strong opinions. There was so much diversity that greatly enriched life as a whole.

I was definitely more popular in Harlem to our male companions. As a result I went on tons of dates and met some great men. One faithful evening I went to one of our local bars with some girlfriends. Right when I walked in, this tall, dark, and handsome man caught my eye. Wow ,I thought, he’s a stunner. The evening went on with across-the-room flirting and cautious smiles. He did not approach me for a conversation though. The evening came to an end and I stood outside the bar waiting for my girlfriends to go home.

Out walks tall, dark, and handsome. This is where the pep talk with myself started. “YOLO Bree! It is now or never. Go talk to him! Do it, do it now!”

I walked over confidently, though I was secretly petrified. I grabbed his cell phone and proceeded to enter my phone number. I saved my number, handed the phone back to him and said, “There you go, now you can call me. My name is Bree.” He was stunned and laughed. He replied, “ Well, thank you, I will certainly call you.”

Well, he called me and we were on a date every evening that following week. Three months later we moved in together. That was two and a half years ago.

Saving my phone number in that cute guy’s phone. Best decision I ever made! I call him Simbo and he’s mine.


Tall Sister, Lets Be Friends!