Dating Magazine

Being Brave

By Datewithcleo @datewcleo

You know that feeling right before you call a girl/guy for the first time? Or that moment at the club when you are about to dance on the stripper pole when no one else is and you’re sober? Or that half-elated, half-nervous feeling when a man you have been eyeing actually starts to approach you?

Being Brave

These tiny instances that we may not even register are times when we are challenging our comfort zones. Unlike getting up early for work, talking to your grandmother on the phone, or having a flat tire on the freeway, these dating and social challenges are a swirl treat of fun, exciting, and thrilling.

Therefore, the latest trend in my life is, being brave. With the help of my goddesses, I want to embrace every opportunity to conquer these thrills and not shy away from dating and social opportunities.

Here are some examples of my successes and failures in the past week.

1. Initiating conversation with random men at a bar.

If in the mood, I am usually capable of initiating conversation with men within close proximity of me and the bar. Strike up a few statements about alcohol, the bartender, or the atmosphere and you are set. (Disclaimer for men, I often do this just because I like socializing and not necessarily because I am “interested.”)

But what if you and your girls are sitting at a cocktail table and you want a specific man or group of men to approach you? This is much more difficult since most LA men are straight-up afraid. Sure, women could make heavy eye contact or approach the men ourselves, but a man that can get over the fear of rejection and go for it is much more attractive… and I should not be blamed for wanting to be attracted.

Of course, a group of pretty girls at a table will get their guaranteed steady flow of completely inebriated men that will sweat, drool, and stare. These men are too be used for entertainment purposes only and then discarded immediately. OR… and then Cleo had an idea. Why not use the bravery of these intoxicated men to our advantage?

As I watched my desired eye candy of the evening decide not to approach us and head toward the exit of the bar, I decided to send highly intoxicated man as savior. “Go tell those guys that we want to talk to them.”

As I saw drunken messenger run off into the distance, lasso the men around the neck, and lead them back to my throne, I could not feel more pleased in my slight act of bravery. Conversation turned out great and I count this evening in my book as a success.

2. Going to a bar dressed up for Halloween when we knew no one else was.

Friday night had the potential for being a costume-night… or not. Risk looking like an idiot or play it safe? Cleo says RISK IT!!

With my dread locks and best effort at Jamaican attire, I tried to spread the Halloween spirit to parts of LA that are “too cool.” I think the plan failed. However, I still had fun and that is what ultimately matters.

Being Brave

3. Confessing my concerns about the dating dynamics between myself and a current male.

This was probably my most challenging task. Usually when I feel a wave of dislike about another’s actions or become concerned about a current situation, I try to take a third person perspective, think rationally, and convince myself to act peaceably in understanding that I can not control people or how they act. (This is another way for saying, I keep my mouth shut.) Unfortunately, in dating this can be very difficult since you can be so invested in another person. This week I decided to voice my opinion within the heat of the moment that, “I am not sure if this is working. The way you speak to me is harsh and I am constantly convincing myself that I can handle it, but I really can’t. As much as I wanted this to work, I may have been wrong.”

Bringing up something like this is risky. The reason I felt ready is because his reaction was not a concern of mince. Whether he acted defensive, sweet, or inexpressive, I needed to get my thoughts out in the open for my own well-being. His reaction would only affirm or deny something I already felt. Huge bravery success for Cleo this week.

4. Singing Karaoke.

With all success comes failure, and in the world of living bravely through karaoke, I failed miserably. Maybe one day I will be ready to step onto the stage, but at this point, no amount of alcohol could help me.


I challenge you all to do things this week that require bravery. No matter how small, overcoming challenges is the best way to reaffirm that there is more to life than the bubble of today.

Happy Halloween,

Queen Cleo


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