Cleo's Dating Blog

Posts Tagged ‘breaking up

What is your passion?

Recently a man twice my age asked me on a date (I said no because gray is not my type, although a Clippers game did sound fun). He prefaced the proposal with this question, “What is your passion?”

As quite possibly the girliest-girl in the world, I naturally responded with, “love.” Of course this includes the love of a lover, but also the love of friends, family, work, the moment, nature, and self. If you were to ask me what I fell in love with most in 2012, it would be how much my patience has grown.

Granted, I still get frustrated and act out (especially when hungry) yet December 25, 2012 yields a person of an entirely different level of patience.

I have work goals, learning Spanish goals, traveling goals, yoga goals, entrepreneurship goals, and body image goals. These are activities I enjoy. However, without a deeper connection, these are just replaceable hobbies to pass the time. I look to give and receive love in all my activities because this is how I feel most fulfilled.


Ironically this combination of seeking loving and having increased patience means I tend to stay in self-sacrificing situations longer than most would… possibly longer than is emotionally healthy at times, as well. I tend to give more than I receive. I tend to expect more than others are willing to give. I tend to give second chances on top of the previous five chances.

Why? Well if I could be a different way, I probably would. It seems easier to be impartial to things and to have a passion more simplistic, like cooking or horseback riding. These things give exactly what you put in. We all know love is a gamble, but none of us seem to know the odds!

I was born a romantic. I study my emotions. I find pleasure in digging deep down to the bottom corner of my heart in as many things as I can. This is where I house my ability to genuinely listen to you when you have a problem, ideas on how I can surprise you with something sweet, determination not to judge you until I know you, and warm energy every time I hug you.

Those who do not do the same often do not make sense to me. Why would you limit your sensations?

I am perplexed until I realize that the consequences can be painful! It is terrible when love is given and not returned or when love is misunderstood and discarded. Every time is a little chip on my heart.

Luckily, the heart need not always be in control. My mind tells me to keep going just as I am. To manifest faith in a sparkly tomorrow in order to keep the chips off my shoulder. To be grateful for Christmas Day with my family and for a promising 2013.

Maybe Santa will not unveil our soulmates today. Or maybe he will. And that is the beauty of an unknown future with endless possibilities.

Warm wishes and Happy Holidays,


One of my favorite past times is sweating. I love when I workout so hard that the sweat stings my eyes and drips into mouth and my shirt clings to my lower back like a sponge. This is purity in its highest form (second to abstinence, of course).

I have been cross-training and interval training for years. Intensity is a word that runs through my mind every time, whether or not I actually push to that level. What keeps me going when my body is hurting is the thought that I probably will not die, even though I feel like it.

Lately I have started to wonder, can your workout mentality leak into other areas of your life?

My theory is: yes.

Much like my exercise regimen, there are times that I tend to “go all out” in my love life and my work life. As if I only have 15 seconds left of spilt-squat jumps, I dig deep for that extra bit of patience, sweetness, ambition, discipline, compassion, or control until even my bones hurt. I ignore the pain and I keep plowing forward. I tell myself that I am not actually going to die.

Sometimes this is good. We all know that getting out of your comfort zone is the only way to accelerate growth.

However, sometimes this is bad. If we push too far past our limit we may sprain our ankle or dislocate our shoulder, in the emotional sense. This can be illustrated by the times when we try to make others jealous on purpose, get too drunk and make inappropriate phone calls, completely lose our sense of judgement, lash out in anger, get moody, get anxious and cry, stir the drama pot, or anything else that could get you casted on a Reality TV show.

Although I may be addicted to that climactic feeling when you finally reach the top of that steep hill in spin class, pushing this hard in your personal life is not sustainable. What is better is to remain consistent.

Taking steps toward your career goals or finding the love of your life is more similar to running a marathon than doing single-leg blurpies. Being ready and then giving up and then being ready and then giving up again is not healthy for any party involved. That is why going slow is always better. Give your endurance some time to build. Let things flow naturally like a pleasant dance and do less forcing.

September will be the month of casting my cares. Will you join me?




As far as I understand, when something does not fit well, you have two choices: shove it in OR give up. I tend to practice both philosophies in my life, mostly out of curiosity.

Sometimes you meet a cute boy and he asks for your phone number. It is new and exciting until he decides to text you for the first time at 3am saying, “Wanna make out?”. Square peg may not even be screwed in properly.

Other times you meet an average looking boy and he surprises you with wit and charm. You have lots of fun together and special exchanges of butterflies. Then you start to think that maybe what you wanted was a triangular peg after all.

You can change your mind all you want, but a triangle is not comfortable inside a circle.

Sometimes you can find bedazzled square pegs. These fancy ones are fun to keep around for entertainment purposes but does not necessarily make them fit better.

Other times you meet square pegs with round edges and it’s such a close match! Attraction, conversation, and availability. Yet something is missing that you can not explain.

And then one day you do find a circle peg! What a rush.

But sometimes the circle peg is not done meeting square holes.

And the cycle begins again.

The good thing is that this time you know how to recognize a circle from a square and you know that trying to make a square fit or trying to make a triangle appealing is just effort without results.

If you are really lucky, then you now also have the experience to realize that all these pegs can not do anything to change your shape, what fits you best, and what you deserve.

To summer flings and more,




Whenever a man/boy/guy/gentleman/dude/douche offers to buy me something, there is always a little voice in the back of my mind that asks, “What will he require in return for this?”

Depending on how well I know the person and what the size of the gesture means to him, I will deduce an appropriate response.

For example, if a poor actor friend offers to take me to a fancy dinner, then I will take that as a grand gesture. On the flip side, if a super wealthy man offers to give me jewels and buy me designer clothes, I will take this as a medium, not-so-serious gesture and if a middle-class guy offers to get me Yogurtland, I will take this as a small gesture. (Offers are real and not fabricated.) Also, a good friend or coworker may not be thinking “SEX” if he buys me some drinks during a night out, but a stranger most likely will be. All of these factors influence my decisions.

Regardless, and I think I speak for most women, the following list are 10 things that women have the hardest time saying “No” to:

10. Would you like some cheesecake? My treat.

9. Would you like to skip the line and enter [insert venue name]  for free?

8. Would you like another skinny-girl margarita?

7. Would you like to go shopping and take my credit card?

6. Would you like me to talk about why all of the other girls around are not as pretty as you are?

5. Would you like some more bread? You are too skinny.

4. Would you like to watch a Ryan Gosling movie?

3. May I Instagram this photo of you and your friends?

2. Would you like to see other people while I patiently wait for you and only you?

1. May I please go down on you? ;)

Be careful of men that abuse our weaknesses! But giving in every once in awhile can be oh so much fun.

Have a playful weekend,


People say this to me often.

“Why don’t you have a boyfriend?” What tends to follow is, “Just lower your standards a little.”

If I could lower my standards and be happy, don’t you think that I would just do it already? It’s not like I am trying to win a contest of who can stay single the longest. I would love to have someone that could watch movies with me and play with my hair.

For those of you that have known me for many years, you know that I have not always had high standards. I used to have lots of boyfriends because I would only look for a few, key qualities and ignore the rest. Usually if a guy was nice and treated me well, then that was enough.

My ability to ignore things has drastically decreased. I can no longer date men that play video games all day, drink themselves to a mushy physique, smell bad, have yellow teeth, embarrass themselves in public, cry a lot, dress like it’s still the 90’s, smoke a lot of “medicine”, have a different personality around friends, have small hands, do not like to cuddle, think driving really fast is cool, have a dry sense of humor, or have nothing interesting to say (these are all true).

I have lowered my standards before, but having the wrong boyfriend is worse than being single and lonely. When single, I spend my time thinking of ways to improve my life. Although occasionally rough for a person like me that loves companionship and the idea of love, at least I know I am improving. When I do not fully adore my boyfriend, my time is spent trying to convince myself that I am happy or that I have enough patience…or else I am thinking of the most strategic ways in which to end the relationship. Sad, I know.

I guess I am at that annoying stage in my life that middle-aged people always tell me to cherish. “I wish I had enjoyed my 20’s more!” Alright, but your 20’s kind of suck when you have no proven career, no authority in the workplace, no family, no money, no beach house, no swimming pool in your backyard, no nanny, and so many distractions. The opportunities are beautiful and boundless, but it is such a waiting game to see which ones will flourish and which ones will crash. One step at a time and hopefully 30 years from now I won’t regret anything major…

Chat soon,



I grew up as an athlete and still carry the same “hard-core” mentality to this day. I do not claim to sit at the top of the bad-ass pyramid, however I dabble in my fair share of physical challenges and can keep up with some of the best.

Despite the half-marathons, ocean swims, and Equinox circuit workouts, the concept of a Mud Run has always interested me. What is not fun about getting dirty and tackling people? Or maybe hiking a mountain would be fun (but only with a guarantee of zero snake encounters). I have other friends that enjoy rock climbing, riding motorcycles, running ultramarathons, or going on wacky juice diets.

As much as I understand the appeal of a good challenge, I can not help but wonder if maybe we are all crazy. Life is already one huge obstacle course! What sense is there in adding MORE?

Living in LA has many challenges of its own. I plan my schedule around rush hour traffic, know that discovering street parking is close to a miracle, find that most people are rude unless trying to get something out of you, frequenting trendy bars and restaurants gets pricey, and most of the hottest men are gay.

Sculpting the body you want is a challenge. Getting over your first love is a challenge. Smiling while at work is a challenge. Being an entrepreneur is a challenge.

Not to mention that DATING is one huge challenge.

So why do we even try? Why don’t we all just eat brown rice and chicken, walk around the block, watch TV, and live alone forever?

Oprah would not accept this of you. This is not living! Being safe and mechanical is a waste of your amazing human brain.

So I am going to stop watching the Mud Run of Love from the sidelines. I am going to stop running circles on the treadmill of the same men. (Can I get an amen?) I am coming out of my dating comma even if that means I need to start online dating, hitting on guys at the gym, burning incense, or praying.

I am currently accepting blind date proposals from trusted sources.

Good luck to you!


Follow me on Instagram! @cleoheartsyou

Sometimes I feel like a big Loser (note the capital letter).

I get caught up in country songs and try to apply them to my life. I want a Prince Charming of my own and I want him to have a big “horse.” I believe you could love me because I am the perfect mix of spicy and sweet. I give second and eighth chances because some people just need more time. And I really mean it when I say I miss you, so it extra sucks when you do not feel the same way.

I feel like a loser because so far my track record is full of endings! Oops! I look forward to things like napping, chai tea lattes, and a good cry. L-O-S-E-R.

But when I look at myself in the mirror, all those feelings melt away. And then it all comes rushing back to me and I remember how smart and successful and fun I am. So obviously I am not the loser, all those other men are!

For some reason I have never been afraid of the “L” (as in Love) word. If it is something I feel, then I am more afraid of not saying it. I can usually handle the rejection because I have so much love to give that my love now is most likely not my last. Unfortunately most people are not this way, so I guess I am a little bit scary! Loser times two.

However, I can not help but wonder if maybe I am just dating the wrong gender. I am pretty sure that my expressions of love and sweet gestures would sweep any lady off of her feet and we could listen to Brad Paisley together and buy “horses” together and talk about feelings and menstruation.

So maybe I am just a Loser because I am not in Love with a Lesbian?

(As a side note, I am fully aware that this post may scare off all men and I am okay with that.)

Do not stop fighting for love ladies and gents because if you do, my chances of finding it are much lower.

Thank you,


Last night I went to a bridal shower. We ate yummy food, said nice things to each other, and smiled a lot. The bride-to-be was glowing. There were gifts. We played games. No one was texting on their phone. No one was downing wine to cut the edge.

Love. What a great thing to celebrate.

However, this got me thinking. We gladly come together for the celebration of love, but what about all the other great things in life? What about independence, freedom, maturity, and security of self? These things are just as hard to find as true love and just as crucial in achieving a happy life.

Thus I propose that we create another reason to celebrate. When a relationship ends and a break-up happens, we should celebrate with a Single’s Shower.

This does not mean bring out the cookie dough tub and cry in it. This does not mean drink until you feel okay with drunk dialing your ex.

Being strong enough to leave a relationship that is not healthy takes courage. Knowing when enough is enough takes wisdom. Refusing to settle for less than what you deserve takes discipline. Loving someone enough to let them go takes selflessness. Ending a relationship without drama takes maturity.

Striving to be courageous, wise, disciplined, selfless, and mature is deserving of a party in my opinion!

We shower the bride with gifts to prepare her for the journey ahead and to celebrate her accomplishments thus far. The single gal should receive the same welcome. The close of a relationship is the start of a new chapter just like that of getting married.

Congregate with friends, snack on salad and finger food, drink moscato, reminisce on how much you have grown up, play games, leave your phone in your purse, and party. You are a liberated and independent person. You are complete and whole whether you are in a relationship or not. Do a little dance. Have faith in the future. Open door number two.

To all the brides and future-brides,


A couple months ago I submitted the following essay to the Modern Love section of the NY times and was REJECTED. And they decided not to tell me why…. I guess it was not boring enough. Hopefully you will like it better than they did! xx, Cleo



I try to be a glass-is-half-full type of person. However when you are chronically single, as I seem to be, remaining optimistic becomes emotionally and mentally tiring. Sulking with a tray of cookie dough and a bottle of wine sounds so much easier.

I have been dating since I realized that I could (sometime back in the 8th grade when I got my braces off), yet for the past year and a half, I have taken a whole new approach to the dating game. Refusing to take a back seat to my love life, I have been on what I like to call, a dating expedition. This journey is based on my philosophy that the sooner I figure out what is it that I want, the faster I can have it. At least, this is the hope.

This whole expedition stems from my inherent impatience and inability to sit around let things happen. I do not do well with passive. “Chilling” is not my forte. Of the role models in my life- Richard Branson, Lance Armstrong, Oprah Winfrey, Lindsay Lohan (just kidding!)- none of them are passive. They take calculated risks, persevere through set backs, and are ultimately successful. Yet, I would almost consider participating in the Tour de France than deal with some of the men I date- key word is almost.

Tall, short, rich, poor, old, or young men are… interesting.

First there was the ex-marine who had no car, confessed how he has gotten four women pregnant, been engaged twice, AND still thought that my early 20-something self would not be scared out of a relationship. Then there was the modern day, heartless tin-man who, after 9 months of commitment-free “hanging out”, admitted that he had never once had real feelings for a woman as he is only capable about thinking of himself during the day. He loves the mental and physical connection (of course), but when confronted about the missing emotional connection, had no comment or idea what I meant. Next came the 30 year old white male who grew up in an affluent community yet still refused to give up his baggy jeans, metal chain-link necklace (ugh!), and wanna-be gangsta mannerisms. In between these men was the hilarious guy from London who flaked on a weekend together 30 minutes before departure, the North Carolina sweetheart who promised to fly me to see him 100 times then fell off the face of the earth, my Miami love from Spain who did nothing wrong but could not combat the cross-country distance, and how could I forget, the couple of model-actors I threw into the mix.

But wait, there’s more. There was the young, successful attorney who begged me to send him pictures… of my toes. The Hollywood club bouncer who name-dropped like no other (as if I should be impressed?) and sent me pictures of him and his gut drinking Coronas. The New York stockbroker who, upon meeting me for the FIRST time, explained how he could tell I orgasm nicely. The security guard who told me everyday that he knew I was eventually going to break his heart… so I had too. The numerous “straight” bartenders that I met at gay bars around the world. The UCLA water polo player with no personality. The finance guy who was MARRIED. The french guy who bought me expensive gifts but never asked me on a date. The medical student who told me, “in a year I would be in love with you,” but never made a move. The loan officer who pursued me solely based on the sound of my voice. The CPA, who against my better judgment, was indeed boring. The twice my age and three times my weight celebrity attorney that sent me long emails about how enchanting I am. And possibly the most interesting, the three different couples throughout the year that were persistent about having a threesome with me (which I safely avoided).

All of this in less than two years is a lot to handle, and I’m sure I blocked out a few from my memory.

I have become what some call a “serial dater.” I usually try to keep between 2 to 5 guys going at one time and cycle through them as necessary. After all, it is never wise to put all your eggs in one basket and any experienced gal knows that most men are a disappointment. Until I find one great man worth committing too, I will continue to date around. However, this does not mean sleep around. My dating and life mantra is: always stay classy.

As my volume of dates shows, my skills at picking up men have grown exponentially. I have mastered the art of eye contact, flirting, and being approachable and have gotten increasingly better at knowing when to call it quits. With each dating experience I am learning how to better recognize the warning signs and having a solid pipeline of prospects makes it easier to cut out these losers and move on. Men are everywhere… I’m just not sure where the good ones are hiding.

Of all the men I have dated in the past year and a half, I have had genuine feelings for about five. And when I say genuine, I mean genuine. I thought about them all the time, wanted nothing more than to be by their side, and wished them well in all areas of life. I was open with my feelings, thoughtful, sexy, fun, listened without agenda, and could honestly see commitment in my future (at least on my end). Initially, being vulnerable does not scare me and the potential of suffering for love has yet to hold me back from diving in. Yet once these feelings develop, I have found that the confident, easy-going woman that I try so hard to be starts to become a hopeless romantic, hanging-on-every-word, love struck kitten. I get soft. Why? Because deep down I am a relationship, all or nothing kind of girl. I melt easily. I love cuddling. I let my guard down before they do. Unfortunately, all five of these men did end up hurting me in some way or another.

Sadly, my naturally loyal, self-sacrificing attitude toward men that I genuinely care for is often interpreted as clingy. Although I have only ever been called clingy (to my face) by one guy, I find the adjective extremely undesirable and derogatory. Thus, I am constantly fighting my instincts in order to survive in this cold, hard world of dating. I force myself not to call. I force myself to be busy. I force myself not to care. I force myself not to give too many compliments or be too sweet. I force myself not to think too far into the future. I force myself not to believe what a man says but to go by actions instead. I force myself not to equate sex with love. I force myself to continue to pursue new prospects even if I do not want to. Force, force, force.

The good thing is, practice makes perfect. I really do live a busy life. I really do think rationally when it comes to men and do not live in a fantasy land. I really am independent. I really do go by actions and not just words. I really do not need or even want a phone call everyday. I really do love myself. I really do believe that I deserve nothing but the best. All I want is to be treated well and, from time to time, shown that I am thought of, cared for, and valued. I want security and consistency. I think this is more than reasonable yet so far, very difficult to find.

Why do so many men associate commitment as analogous to prison? Is love really that suffocating? Maybe I get too excited.

Although I have and continue to battle my naturally lovey-dovey, hopeless romantic, “clingy” behavior, there are some things I still cling to that I will not compromise. I cling to the idea of love and the idea of one day having my own fairy tale. I cling to never settling for less. I cling to good first kisses. I cling to the belief that not all men cheat. I cling to the hope that marriage is not just hard work, as most couples make it seem like, but a beautiful partnership. I cling to true love lasting a lifetime. I cling to my perfect man being out there somewhere. I cling to waking up smiling everyday. Yes, I am clingy and I always will be.


Posted on: March 31, 2011

I have been giggling a lot lately, almost uncontrollably. Just giggling over silly comments and random thoughts all throughout the day. Even at 7am when I am barely awake, 2:00pm when my coffee is wearing off, and 11:30pm when I am dead tired, I am still giggling.

If you read my last few posts (or if you know me personally and have seen and talked to me), you may have noticed that my spirits have been down the past couple weeks. My feet have been dragging, my eyes not so sparkly, my smile often fake as hell, and my head lifted slightly less high. Actually, I hope you noticed because I made it obvious! I can never hide anything I feel, even though sometimes I try. I wear my emotions on my sleeve, and always have since I was just a little Cleo. Overall, I prefer to live this way because there is no guessing involved.

Thus my friends, or people with strong interpersonal intuition, do not find it challenging to see when I am suffering from heartache or when my love life is not aligned. When this Libra is out of balance, you know. I like to think of it as being genuine.

While I was out of my emotional element, I viewed this time as one of those temporary but inevitable phases of life. Dating is difficult and seldom works out as predicted (or at least that’s how it is for me!). The healing process is a waiting game. Learning to be without someone who you adored is hard. Trying to forget that you miss them is hard. Being sad is hard. However, it becomes increasingly more difficult to cope when you have not fully set free the idea of being together. Dabbling in that gray area where you are kind of dating and kind of not is emotionally tangling. I was tangled for a long time.

So, after almost a month of tangling, I made a clean break. Go me! As you know, I am not new to this dating thing, so I knew that if I kept stringing myself along (or letting myself be strung along), then my resentment would grow to outweigh any potential positives. Once you decide to make a clean break from the past and cut all emotional, physical, and social ties from a past love interest, the healing process is much faster. However, make sure you are ready and fully accepting of the high possibility that you will never be together again. Take time in making this decision. When you are ready, you will know.

You can imagine my elation when I realized, just three days after setting myself free, that I was giggling, and giggling a lot. Finally I feel like me again! At first I didn’t even notice. It is almost like taking 3 shots of tequila in a row and then a few minutes later it hits you all at once and you are shocked (not that I have ever done this, hehe). The feeling sneaks up on you! Even if you have taken the necessary steps to get there, the magnitude of the feeling is still unexpected.

It is the light at the end of the tunnel that a few weeks ago, I was not sure existed. But it does! And it is so bright and warm and liberating. No matter how much you are struggling, you will feel amazing again. Be patient, nurture yourself, and make the tough decisions that will benefit you in the long run.

Until next time,