Cleo's Dating Blog

Archive for the ‘Questions for Cleo’ Category

Here is a poem I edited for a friend, aka Poison. Collaboration leads to beautiful things.


Life is not without intense difficulty and tribulation,
But understanding emotion is the most painful of all.
Love and anger are what make the world turn.
In love is the possibility of deep pain,
yet without love, there is deep anger!
there is no way but forward.
There is no going back,
there is no stopping time.
When we reflect on the past,
we try to give emotion to life.
Yet are these emotions even real or justified?
Life may be painful,
but at least it is consistent.

We all have a routine. Whether you snooze for thirty minutes until you finally peal out of bed, hop in the shower, and book it to work (that’s me!), or if you sleep until the sun forces your eyes open, go for a jog, and have some grapefruit juice, we all start making choices as soon as we are conscious. We chose what we wear, if we smile at the security guard in the lobby, how fast we drive, and how much we day-dream.

But how many of our choices are influenced by our mood? It takes a lot of effort to smile when you don’t feel like it, to listen when you are preoccupied, and to laugh when you feel sad. Most of my day requires me to be positive. I must serve guests and my bosses with a smile and a skip in my step- after all, that’s why I was hired. I must listen, laugh, and care about my friends because I want to keep them around. I must be fun to date because I do not want to end up a spinster cat lady. Thus, many times when my day or my work week ends, I am more emotionally tired than anything.

I’m sure we all know people that we would classify as “bi-polar.” Whether clinically diagnosed or not, these people are cheery one moment and erupting with anger the next. Hot and then cold. Their emotions are like a pin ball machine and being around them is a gamble- you never know what could happen! My theory, as cheesy as it may sound, is that this occurs due to love.

I have a beautiful friend who recently asked me, “Do you think being in love gives you more of a reason to want to wake up and seize the day?”. I would definitely say yes. And, you don’t even need to be “in love” to feel love. Think back to the last time you felt head over heels for someone… the electricity of being close, the passion, the urge to giggle even when nothing is happening. And remember how bright the sun was that day and how vibrant the flowers were? I swear, food tastes better, jokes are more hilarious, and work is more fun when love is present. The little things become so special, like hearing someone’s voice, holding their hand, or simply recalling a recent memory. Sleep is more restful and it is not as hard to wake up the morning. Daily life has flavor and the routine is no longer mundane. You feel powerful and like conquering everything.

If you felt love, would you be as quick to be angry? Feeling love makes me glow too much to be angry.

Knowing this makes me want to be a little nicer to everyone. Like a two-sided coin, with love comes the anguish or absence of love. The lack of motivation to get out of bed, the dragging of your feet from place to place, doing the minimum to get by, and the longing to be numb and just do nothing. The beach doesn’t even look beautiful anymore, the sky may as well be gray. All food tastes like cold oatmeal. Flowers are annoying and overrated. You are always tired. People talk too much. Hate everything.

Love is hard to find and is often, completely out of our control. We all try our best, but not all of us play the right cards or have the same luck. Some of us are not as affected by love and heartache as others… some are better at hiding pain than others. I know that I suck at it! Everyone always knows when I am struggling. What helps me is remembering that we all go through disappointments and we all have down days. The good thing is that these feelings are cyclical and won’t last forever! Talking with good friends helps a lot. What is really important is to spend time everyday reflecting- reflect on who you are, what you want out of love, and why this moment of happiness or sadness is merely a step toward your ultimate goal. That the all-encompassing, body-consuming feeling of good love is worth it. Why would you want to live a life without flavor?? Keep trying. You will find it again. Mommy Cleo says so.

Love you all!


Disclaimer: This post is for mature audiences only. I am going to do my best to be straight forward and honest with this subject- although it may be challenging since I am abstinent and waiting until marriage (as of yesterday… maybe, hehe).

A man friend recently requested that I write about what every man wants to know most, which is, “what is the best time to first have sex with a new girl?”

This subject reminds me of a Mike Posner song, Bow Chicka Wow Wow. Here are some of the lyrics:

Are you tryna make me late, wait wait till the second day
But I cant cant cant even contemplate
Waiting one more minute, lemme jump in it
I brought you flowers and a teddy

You’ve been playin naughty, getting with me all night
We both know exactly what you want right
Tell me what you want though
Tell me what you gon’ do…

The song illustrates well the battle between men, women, and sex. First, the female is acting naughty, sexy, flirty and sending signals of wanting to “get down” to the male. Male takes signals literally and buys flowers and teddy to ensure that the deed occurs- simply following a social norm. However, since women are complex beings, it is more likely that the female wants only to be lusted after but does not actually want to engage in the lustful act (at this time), as shown by her wanting to wait in the song. Male can not wait. Thus he is going to keep trying and trying and trying.

So we have a minor dilemma and a compromise is needed. Man may ask, “sex feels good, why would a girl even want to wait?”

First, some preliminary questions?

1. Are you and your female on the same level of attractiveness? Often women give off mixed signals simply for attention, for the fun of it, or to be friendly. I know because sometimes I am guilty of this and I have to ask myself, “wait, what impression is this guy getting? do I really want to rip his clothes off?” More often than not (like 95% of the time) the answer is “NO” and I consequently need to readjust my actions. Ladies, be careful what signals you are sending.

2. Are you a trustworthy person? A semi-experienced gal knows that sex is better if there is some level of trust and emotional connection. If a guy does not seem genuine, his chances of getting laid are much lower (unless alcohol, lavish gifts, etc are involved). Thus a man could ask himself, “what level or amount of effort have I put into courtship?” If the answer is “minimal” than any self-respecting girl would give you minimal amounts of playtime. As a side note, courtship does not equal expensive dinners or long talks on the phone. The easiest yet most important forms of courtship include listening well, paying attention, being thoughtful, texting back in a timely manner, and not being too aggressive. Excessive peer pressure is never necessary.

3. Do your intentions match the type of girl you are going after? I will not be the first to cast a stone at someone with the sole intention of getting laid. Being straight forward with yourself and you sex prey is important. However, if that is your intention, then a classy girl, like Cleo for example, would be the wrong person to go after. Make sure you choose wisely.

Alright, so you are a good match and you like the girl… now what? As a a general rule, i’d say waiting anywhere from 1 week to 1 month is reasonable. Of course it also depends on how often you see each other and when your/her last relationship was. It also helps if you can gauge whether or not she is “seeing” anyone else at the time. Do not be too quick to assume that you are her #1. Sloppy seconds or thirds never feels as good (from what I hear) and a good girl only goes with one at a time. When you start to feel like Mike Posner and that you just can not wait one more moment, bring up the subject to her. Sex is natural and should not be considered taboo. The more often you talk about it in a tasteful manner, the easier and more comfortable it is to bring up in conversation. I personally think it’s fun! hehe

Ladies… how do you know if sex is the right choice? Do you want to wait but sometimes it seems easier to just give in so the guy will stop trying so hard?? Let’s be honest, men can be really annoying. Sadly, that is never a good enough reason to give it up.

Here is what I find to be true:

– Sex without emotions is just as good as sex by myself… and sex by myself is much less risky!

– Sex too early with a guy (thus, without having any real emotions) is not going to be great. It may be fun at the moment, but the next day you will think, “ehh.” My roommate describes the feeling as having an emotional disconnect from yourself. If the sex does not feel right, then I do not feel right. And if I am dating a guy that does not make me feel like myself, then I will want to find another.

– Faking emotions to have good sex is only harmful in the long run. This is when you can become wrongfully attached to a man that in reality, you probably do not even like.

– Pretending the guy is someone else is just rude (oops). And if you are really good at it, this can also lead to wrongful attachment.

– If you lead a man on too much, you become a bitch if you do not properly “take care of” the consequences.

– Good sex is worth the wait… a good man even more so.

Basically, when it comes to deciding what is the right time for sex, you must follow your gut feeling and not any other body part (not even your brain). Your mind can trick you into believing what you want, i.e. “I know he is in love with me,” when it has been two weeks or “he told me he only cheated that one time so I trust him again,” when you know deep down that’s absurd or “she gave me her phone number so I know she wants me,” which is just wrong.

So be smart (and safe) with sex and have fun!! And as always, let me and the readers know what you find to be true.

Love you,


Due to popular request, this post covers the concept of age and its relevance in dating. Does Age Matter?

When I was younger I always thought that the answer to this question was, “yes, duhh.” However, as the years seem to fly by (*tear*) so has my opinion on this issue. I can remember a distinct moment when my unwavering “yes” began to tumble .

About a year ago I started a new job. This meant new coworkers. One of my coworkers was a 25-year-old hottie who had been dating a guy for over 3 years. Naturally curious, Cleo wanted to know details. Long story short, turns out he is over 10 years older! My first thought was “yikes.” But since I try my best to avoid casting unfair, premature judgment on people, I wanted to meet him and give him a chance.

Have you ever spent hours on a puzzle and you just can’t get the godforsaken cloud pieces to fit? Well seeing them together was like finding the last piece- such a beautiful combination.  That was when I realized that it is not necessarily age that matters,  but rather someone’s maturity level or “inner” age.

Everyone is different and everyone matures at a different level. I think of “inner” age as the age someone most identifies with. I, for example, believe I have an “old-soul” and my maturity level is probably three to five years older than my actual age.  I enjoy hobbies, conversations, and responsibilities that vary from what most individuals my age enjoy. I feel most comfortable around people who are older and generally have trouble staying stimulated with those younger (there are exceptions however, my bff is a few years younger… but he has an old soul as well).

I got my first major taste of “inner” age at the beginning of 2010. Since dating is a journey and trying new things is important in determining your true interests, I dated two men (at different times) at the beginning of the year who were over 8 years older- my largest gap (so far hehe). I was tired of the lack of maturity, commitment, financial establishment, and creativity of boys (yes, boys) my age. Well… somehow I managed to find two of the most immature older men. After a few dates, I asked both men what they believe their true, “inner” age was and they were both at least 6 years younger at heart. Being immature is normal and acceptable… just not for me or the men I date. I’m sorry but if I am going to date a significantly older man, he better own a car, rent more than just a sh*tty apartment, and not dress like a high school senior that wants to be a gangsta. Peace out homie.

The Situation from the reality show Jersey Shore is a prime example of a guy with a much lower maturity level. Yes, he makes bank, but being 30 and still getting wasted, banging girls, and being annoyingly irresponsible is just not attractive to a classy lady.

Now that I think about it, at least three additional men this year that I have dated identify their “inner” age as being years younger than their actual. Maybe this is a Los Angeles thing? Time to move! hehe.

Now you may be thinking, why is maturity important? Isn’t dating just about having fun and enjoying the moment? Surrounding yourself with individuals of equal or greater maturity levels helps you to grow and mature yourself. Mature individuals also tend to be better and more reliable friends and boy friends. Especially as young adults, hanging with the wrong crowd could drastically shape your future. One avid blog follower recently asked, “Why is there often such a disconnect between people’s actions compared to their words?” I believe the main problem is a lack of maturity.

Before I continue, I fear that my last statement will cause readers to believe that those who are slower developers/less mature are in turn less intelligent or less important people. That is entirely untrue. Cleo’s followers must always remember to treat all people with respect no matter their maturity level… but that does not mean you need to date them!

Lack of maturity yields a lack of responsibility. Side effects of a lack of responsibility are frequent occurrences of flakiness, continually making empty promises, selfishness, moodiness, irrationality and/or rudeness. Basically these types of people:

I could probably write a whole post on why Mel Gibson is not What Women Want, but I shall refrain. Women want consistency. If you are going to be an a**hole or a d*bag, then be one all the time so we know for sure. If you are going to promise something, then follow through. If you say you miss someone, then act like it consistently. Do not pretend to be something you are not or to feel something that you don’t.

On the other hand, if you notice that you have a tendency to treat people in varying cycles depending on the day or pull of the moon, reevaluate your own maturity level. You do NOT have to be mature. Just don’t act in a way that is contradicting. Know you’re own “inner” age.

People are people and will forever make mistakes. The best way to limit making mistakes is by being honest with yourself first, and then those around you. If you are stressed out with your life be upfront about it, don’t fake calmness and then suddenly catch Turrets. No one will want to be around someone who makes them feel as though they are walking on eggshells. You will be 38, renting an apartment, still single, and fat because you turned to food to make you happy. Real happiness is in growing, learning the ways of maturity, taking accountability for your actions, and thus fostering quality relationships. If you practice, you can be confident in your ability to be a well-balanced, centered adult and know that if a relationship ends, you were honest and thus have nothing to regret.

Most importantly, if you are dating someone who shows signs of being on a different maturity level then you would hope, take note of your gut feeling and try not to ignore it. A potential dater’s age is not a good determinant for how maturely they will treat you. Instead, look at their actions and how well they correlate with their words. The larger the discrepancy, the lower the maturity.

Good Luck!

Much love,