Letting Go of The Playboy

Who said letting go is easy? Who said falling in love with a playboy who loves lotsa girls is easy? Both situations are never easy – never fail to bring tears at our very eyes.


This is a story of a friend who happened to fall in love with a resident playboy at the school.

The Characters

This is a story of a friend with guys named Drew a.k.a “The playboy slash jerk” and Mike a.k.a “The shoulder to cry on man”. Let’s add some spice and make this story somewhat more complicated. Meet Steph a.k.a “The devil in disguise”. She looks like an eye candy to everybody else (especially the boys), yet to me and to my friend, she’s just another eyesore.

And meet my friend, Caitlin. She’s smart, talented and pretty – she’s the closest word to perfection. I’m not saying these because she’s a friend. Ask others and they will answer the same.

Drew, the guy who’s been linked with every other girl in school – hot girls. Mind it, hot girls. Rumors have it that he changes girlfriend every month, or rather, every week. According to him from the short (but serious) talks we had, he believes that everyone has its own imperfections – him, being a playboy is an example. He said that he has “confidential” reasons why he is one. He looks like a jerk, but actually, he’s just another man that needs a soul searching (I know it). The only thing (i guess, except for his looks) that makes girls flock around him is when he starts talking..seriously. It’s like sugar and spice combined. Sense and humor. No boring moments with him. He’s just another crazy guy – that needs his own crazy girl.

Mike doesn’t look like a shoulder. He doesn’t look a bit like one. He’s my friend’s crying shoulder at times of sadness, painful sceneries and hurtful feelings. As just another story would tell, he is the Jerk’s bestfriend – with a capital B. He also got the looks, moreover, he also has the brains. I have no idea why girls don’t flock around him unlike to his bestfriend. Maybe it’s because Mike is the silent type of guy? Maybe it’s because Mike is somewhat serious in life and doesn’t kid around that much? Maybe that’s why. And also, because everyone knows that Mike has secret feelings for his bestfriend’s girlfriend (even the Jerk knows it).

If there’s a person who would be perfectly fit to be described as ”flirt”, I would volunteer Steph. No questions, no other nominations, no other contenders – she would definitely win the crown (in fact, she already did). She’s the hottest babe around the campus, the girl version of Jerk. They might have been made for each other. Fortunately, they weren’t. She thinks she’s an eye candy. But she’s an eyesore. Everyone thinks of it the same way about her. An eyesore that needs to be applied by an Eyemo or a Vision or any liquid medicines for the eyes. A sweet fact: she’s Mike’s ex girlfriend. Unbelievable? Indeed. That’s why it is still a puzzle to me how they (especially Mike) fell in love with each other. Guess the phrase ‘opposite attracts’ does apply to them. She dumped Mike and with that, I couldn’t thank her enough.

The Conflict

My friend, Caitlin, met Drew at a party held by the SSG in the 4-corner walls of the Drake Bldg. Having the beauty of a princess, they clicked and swooossh – exhanged numbers and messages at the next evenings of their lives. I told my friend to be careful about that Drew guy as he won the award of being the ‘Playboy of the Year’ and he lived to it proudly. But Caitlin never heed to my advice and to the advice of every person in the school and outside of school. She said that she would never get into a relationship with the Jerk whatsoever. She told us that she isn’t insane yet to risk her heart getting broke into pieces. We were relieved.

Then came Mike, whom we’ve known before because of his too much exposure – joining contests and etc. It took him so long to realize (after a breakup) with Steph that he can have a chance at his bestfriend’s girlfriend. Back then though, Jerk and Caitlin were still on the ‘courting’ stage.

Two months was a record breaking for Drew. He wooed Caitlin for two months, and we, ourselves couldn’t believe at the fact that he really did. Whenever we sit at the Acacia Tree just outside of the library at noon time to review some notes, Drew would be there with Caitlin strumming his guitar. I know some of the girls are really jealous at our friend’s fate – even us. But what can we do? I guess Caitlin deserves someone like him – minus the playboy part.

Anyway, on the other side of the campus was Mike. He just broke up with ‘eyesore’ and we started going out. I don’t know why I said ‘yes’ when he asked me out when I certainly know that he’s diggin’ my bestfriend Caitlin. Okay.. so we went out, did crazy stuffs together, talked about anything under the sun and I finally came to a conclusion that the stone-looking Mike is not stoned at all. HEEHEE. At those times too, he pleaded some help for my friend. XD But then, I also knew that Steph wasn’t as detach as an oil and water to him. And I also find out that the two are still going out – thus answering him my firm NO. I was thinking that he should at least clear his mind and heart first before courting Caitlin.

The Climax

Caitlin and Drew got together and Mike bled his heart out. He stayed quiet and silent about his feelings though. Kudos to him for keeping it up. The relationship between a friend and a playboy seemed well and really smooth for the first two weeks – again, another record breaking for having a relationship with ONLY ONE GIRL that exceeded a week. But things got a little rough when Drew started hanging out with Steph and company. Caitlin never says anything about the topic – the rumors – and everything else. She just sits silently – observing and analyzing every detail of what was going on. Another attitude that I really like about her. After a month, Drew started to stop communicating with her. He never calls, texts or goes out with her anymore. We knew Caitlin felt so much pain – but we never ever seen tears and heard rants about it from her. Whenever we ask her what she thinks about it (the relationship and Drew), she would just smile and answer us cheerfully: Everything’s fine. She expects us to believe that? Yeeeaa, right.

Two more months and the relationship was somewhat ‘cut off’. Drew is back to his everyday life as a playboy – flirting with every hot girl in different corners and hanging out the with the flirstest of them all.. Steph. That was when we told and suggested that Caitlin should take a move and break up with him – officially. That was when a rumor came in.

The Jerk’s bestfriend is going out with the Jerk’s invisible girlfriend.

Shocked them – not me. I knew this was going to happen. I knew Caitlin would find some outlets. I knew someday, Mike would have the guts and chance to confess. And I really think at this point of time, they do need each other.

The Jerk was alarmed and stormed to ask Caitlin and Mike about it. Mike stood there – silent. Caitlin beside him, frozen. Steph looking at Mike, unbelieving. Drew clenched his jaw and looked at Caitlin.

“It’s true then.” Everyone dropped their jaw at what we saw in Drew.
He looked so hurt and so.. a different Drew. They broke up. He stormed off. Caitlin ran after him. And for the first time ever, she had said something.

“I’d hate you.. if I didn’t love you this much.”

The Conclusion

Mike seemed to realize that he doesn’t have any chance at the Jerk’s girlfriend. As to what I’ve heard, Steph reconciled with him and started a new relationship. Caitlin told us that he still sends text messages, FS comments and IMs.. but he clearly said that it all ends there. No feelings attached.

Lesson learned: Never take a man for a shoulder to cry on while you are still in a relationship, that would leave him confused and hurt.

Drew and Caitlin? They broke up but everyone still knows that they still got feelings for each other.Caitlin is still silent to us about what she thinks of the whole thing, but we respect her for that. And I think there’s nothing wrong with it; after all, love is defined subjectively. Each and everyone of us has its own meaning for it. What they have now is a relationship that those two can only define. No commitments but fulfilling.

Lessons learned: Letting go is never easy – especially if you love someone that you can’t even hate them enough. You know if you love too much if you can feel happiness despite the pain. And yes, letting go and falling in love with a playboy are both situations that will always have something in common.

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