Friday, September 24, 2010

Twisted Sister

Dear Chuck,

I’m 22 and my brother is 23 (I know, my parents didn’t mess around). He is blessed with having some of the best looking friends who also happen to be really great guys as well. His best friend (let’s call him Toby) is gorgeous and I think there is definite chemistry between us. My question to you Chuck is whether or not I should speak to my brother about getting together with Toby. My brother and i have a great relationship and he isn’t the over protective type at all.



Dear Charlie,

Jesus, nothing like having quality beef paraded for free through your families lounge room! It must feel like you’re at an all you can eat smorgasbord – so many fine offerings in front of you, ready for your consumption. Chuck bets it makes your mouth (and other areas) water with anticipation.


Let Chuck put this bluntly; if you hook up with your brother’s best friend in any way, shape or form, you are effectively driving a steak through the heart of your brother’s friendship. Let Chuck step you through this:

Chuck’s awesome point number 1: No matter how cool of a guy your brother is or how great your relationship is, there is no possible way that he is going to be comfortable allowing his mate to carve up his sister. Charlie, you need to remember that he hangs with these guys on a day to day basis so he knows what goes down. There are no non Mormon males at 23 years of age who don’t spend at least 50% of their time either having sex, trying to get sex, talking about sex or thinking about sex (that figure is likely conservative). In fact even Mormon males are doing that, it’s just that they are doing it within the confines of a marriage they entered into at 21 and with at least 2 kids. The reason they got married so young was so that they could actually have sex without God smiting them. Anyway, Chuck digresses.

No matter how sweetness and light these guys come across in your presence, the reality is that they are chasing minge at all times and your bro knows this. Granted, they may be a classier bunch than your average 23 year old males, but they’re males none the less. He will not feel good letting one of his boys be with his sister because he knows better than anyone what this guy is after. It won’t sit well with him.

Chuck’s awesome point number 2: Being an older brother, he is genetically engineered to be protective of you and your interests. No normal older brother will willingly consent to any of his associates entering the holiest of holies of his sister. In fact, he is likely to be genuinely pissed at anyone for trying to penetrate you.

This protection gene is less dominant if the sister is older. Effectively your parents have fucked you by having him first because if you were older you would face less resistance from him if you had a crack at his buddy. Simply by being older turns the responsibility tables and he doesn’t have to watch out for you as much. Blame your folks for you missing out on boning his hot pals.

Chuck’s awesome point number 3: If you do manage to hook it up with Toby, how on earth do you think he’ll be able to hang out with your brother again? You guys may have a great relationship, but do you really think your bro wants you tagging along to everything he does with his mates? Conversely, he isn’t going to want to be with you and Toby while you canoodle and dry hump (unless of course you guys have a REALLY good relationship).

All of a sudden your business and his business get mixed up and as they say, you should never mix business with pleasure.

Chuck’s awesome point number 4: Despite being best friends, dudes need space. Whereas he could once kick it with Toby on a ‘needs’ basis, now Toby is around for family barbeques, Christmas and other special occasions. Its friend overload and the thing that will give is the friendship.

Chuck’s awesome point number 5: You’re only a young pup Charlie so the likelihood of this relationship standing the test of time is slim. With that in mind, where will your brother stand at the moment of reckoning – the breakup? If you were mutual friends and one of you commits a deplorable act, then it is common sense that the 3rd party (your bro) would side with the person who got shafted. Blood is thicker than water however and he is almost obligated to side with you even if you turn out to be a nut job who made Toby’s life miserable. The break up will totally torch his friendship because even if it is amicable, it will still be difficult to have Toby around you and vice versa.

Chuck’s awesome point number 6: Trust. If you make a play at one of your brothers boy’s, he is always going to wonder if you’ll end up working through the entire group. Imagine how embarrassing that will be at your eventual wedding when a large proportion of the male crowd are saluting the fact that they’ve chopped you up. At the moment your brother probably has no idea that you’re interested in his mate. If you make a play, he’ll forever have his head on a swivel, checking to see if you’re ready to swoop in and attack the rest of his posse.

Chuck’s awesome point number 7: Chuck doesn’t enjoy being a naysayer so let’s consider how you could make this work.




Ok, so even Chuck’s big brain is struggling to help here. About the only possible way this coupling could happen without destroying your brothers friendship is if you hold off and wait until your brother is either in a serious long term relationship or better yet, married. The reason for this is that when your brother settles down himself, there will be loosening of the time he spends with his buddies and his priorities will shift to family. You hooking up with Toby will lessen the impact on his social life to a degree and therefore he will be less concerned. Having said that, all of the above issues Chuck pointed out still apply although muted in each instance.

So in all reality, you and Toby hooking up is a bad thing for your brother and his friendship. Trying to talk to your brother about it will not help the situation at all since he either flat out say no which will piss you off or he’ll get uncomfortable, not say anything and let you go ahead with it. He will then spend the rest of your relationship with Toby trying to passively aggressively ruin it. This will damage your relationship and his bromance with Toby.

If you are desperate to get your freak on with Toby, get devious and buy him a long overseas holiday for his birthday (after talking up how he should get out and explore the world) and pounce on his bestie the minute the international departure gate closes! You’ll have all of the above problems, but you’ll have plenty of time to figure out excuses or solutions.

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