Olivia Jaramillo

Saturday, today is the day. I have a date with John! I am equally excited and nervous. I can see it in my head, I am going to look spectacular, and everyone will be looking at me. Men will want to be with me and women will want to be me. I am sure I will turn every single head as I walk from my car to the Martini bar. As soon as John sees me his jaw will drop, he won’t be able to stop smiling and looking at me. Surely it will be a great night of laughing, flirting, and feeling gorgeous. Sure, it must be? It has to be! Otherwise, what is it going to be? Will we not connect? What if he sees me and walks away? What if I do turn heads but for the wrong reasons? What if every single person clocks me as I walk by? Suddenly, just like that, I am crippled with fear and I doubt everything I worked for all week. I built myself up for this day, for this moment to create an amazing experience, yet here I am feeling slightly foolish. I’ve gone from Adriana Lima strutting down the streets as my runway to a bumbling afterimage of myself. Doubt has once again crippled the inner Mexican goddess and replaced her with a weak scared self-doubting version of myself.


I had to snap out of it. It had taken a long time to get my confidence this high, and I was not going to let my insecurities get me down or make me cancel tonight. Just a year ago there was no way I would have even considered dating, and now here I was on the cusp of kicking off Olivia’s wild adventures. In early days of transition, I still had to keep my number one on the sides and back of my hair. I was never comfortable with relying on wigs; it was just not part of me and made me feel uncomfortable (I do realize extensions aren’t comfortable either but they feel more natural).

Breathe in, breathe out, the woman staring back at me in the mirror took those breaths, and slowly exhaled, and got to work on makeup. I started early; it took me two hours! I recalled all past experiences trying to put makeup on, and this time around I was going to be 100% sure not to make the common mistakes. Enrique Iglesias and his sexy voice played from my Echo as I applied my primer and all my other products. My hair was semi-done. I had combed it and only needed to add curls and some texture. Thanks to my very best friend (a beautiful Dominican Cis-girl), my makeup skills had tremendously improved and when I was all done. I marveled at how great I looked! I finished my hair, put on my black jeans over my blue sleeveless bodysuit, strapped on my heels, and took a look in the mirror at the finished product.

Skip to arriving at the restaurant. Confidently, I strut towards the restaurant bar door, which is located in a fancy outdoor shopping center. A man standing by the door sees me coming, and he immediately opens the door for me. I give him a smile and a thank you, and he smiles and says I am welcome. The three girls working as valets are all standing looking at me, I can tell they are a bit astonished at how tall I am (almost 6'5" in these heels). However, this tall girl gives them a confident smile. They point me towards the bar, and leaving them behind as I start walking that way. I can tell I am turning heads, for good or bad reason. I don’t know, and I don’t care. What I do know is that I feel good, I feel like a woman.


I see John at the bar. Yep he looks just like his pictures on Bumble. He stands up to greet me, gives me a hug, he smells so fresh and oaky. He compliments my looks, saying I am beautiful, which makes me smile in the most strangest of ways, something I hadn’t felt in a long time. John has such a nice smile and bright baby blue eyes. We order drinks, and we talk and talk for over two hours. It was only then that we realized we had lost track of time. As we get ready to leave he puts his arm out so I can hold him by his arm, and he leads us out of the restaurant. I could tell he felt good being held by me and leading me out for all to see. I look composed and cool on the outside but on the inside, I am so giddy and excited! He walks me to my truck, where we say we want to do this again, and we share a great kiss good night.

Success would you agree? It all sounded rather easy didn’t it? Well as you and I know it isn’t that easy. It takes enormous courage to not only transition, but to go out in public. Transitioning made me feel completely exposed, as if I am bearing my heart and soul for the world to see and judge. I used to spend entire dates comparing myself to other cis women walking by or the waitress taking our order. I would even go as far as comparing my hands to my date’s hands!

But why be so shy and unassertive? I am never going to be a cis woman. I am a transgender woman, and there’s nothing I can do about that. There’s only one thing I can be, and that is be the most beautiful Olivia that I can possibly be. So here is what I have learned:

Confidence truly is your best friend. You will never be that transgender supermodel you follow on Instagram. Be confident in being the best person you can make of yourself. Fall in love with the way you do your makeup, with the contours of your face and the shape of your body. Believe me, just as we look at others and want their looks, there are others who look at us and want our looks too.

Give yourself a break. Ok, so you still wear wigs, or maybe that bind doesn’t help you as much as you wish it did. Its fine, remember how long you have been transitioning and that there is still road ahead and that you will get there in terms of what you want your body to achieve. In the meantime, envision that successful path and you will get there!

Truly ask yourself if you’re ready to date. How far along in your transition are you? Do you feel confident enough in yourself to go get groceries yet? Are you secure enough to meet someone who might have looked at your photos that you sort of manipulated how big your breasts truly are or how flat your chest is (for trans men)? Believe it or not these things are important, just as we want others to treat us with respect, let's respect others by being honest of ourselves. I realize we all want to rush and get to that fairy tale point of our transition, but be patient.

Have you been single long enough? Sometimes it’s important to be alone and get to know ourselves. Maybe you just broke up from a long-term relationship, and miss companionship. Don’t rush into something just for the sake of it, be in a relationship with yourself; fall in love with yourself!

Who exactly are you looking to date? If you have always considered yourself “straight" but now want to try and feel like your correct gender by dating the opposite gender, think if this is really something you want. What exactly is your dating demographic? That’s for you to answer.

In the meantime, follow me on entering this crazy world of dating. There’s as many crazy characters in dating land as in Alice’s wonderland! And for you, one step at a time, smile, and be confident. You are headed in the right direction! You will get there, and you won’t even realize it.


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