An unsolicited letter of advice to Jessica Simpson

By Phin in Jessica Simpson, Portia de Rossi

Darling Jessica,

We all realize you’re very upset that you scare men away on a seemingly regular basis. It must really be a blow to your seemingly infallible self-image and a swift kick in the nuts to your self-esteem.

Trust me when I say that it’s not that you’re “too hard to be in love with” as you told Ellen DeGeneres. Your romantic exploits that end up on the cover of tabloids would be a welcome popularity boost to some previously unheard of no-talent hack, look what Britney Spears did for Cleatus Federline’s career. Whilst you may be “a lot to take on” I’d be willing to bet there are a large number of men “up” for the challenge, if you know what I mean and I think you do.

So Jessica lets drop the whoa is me pity bit. If you’re ready to be in a relationship I’m sure some schmuck, myself included if’n I weren’t happily married, would be more than willing to succumb to your evil ways and cater to your every whim, you just have to “get back out there”.

Let me be the first to recommend one of the on-line dating sites. I’d skip e-harmony and match.com though. They’re way over-rated and a bit too overly publicized, maybe the Yahoo! Personals since they’ll let you post “adult” photos. Of course that we’ll have to find a way to draw attention away from the 2,000 other chics already using your pictures in their profiles, so let me suggest a series of tasteful* nudes for your profile. Hell I’ll even volunteer to take the pictures, we wouldn’t want them being leaked all over the Internets.

One we get your profile online we’ll need a way to thin out the herd of potential suitors. We’ll start by getting rid of anyone who’s been in a “Boy Band” or is named John Mayer, since they’re unable to handle the stress of sleeping being with you and are by default gay or at the bare minimum they sit down to pee. I’d recommend we look to other starlets who are successful in love. We’ll skip the true love Britney found with Cleatus, we should find a happier couple. Perhaps Kate Moss and her pet project / train-wreck Pete Doherty would be a great role model. Or maybe you’d prefer someone a bit more high-brow like Lindsay Lohan’s beau Harry Morton. Just make sure whoever you choose has the stones to say no to a sequel of The Newly Weds.

We have faith in you Jess, if we may be so bold as to call you Jess, really we do. We know that your one true love is out there, just quit dating candy-asses and find yourself a real man, like me or Matthew McConaughey, when he’s not out chubby chasing.

I just hope your incessant whining on Ellen wasn’t an attempt to lure her away from Portia de Rossi. ’cause while I, and 99.5% of our male audience, are all for you getting your lesbian groove on, if it involves Ellen it’s the bad gay, kind of.

Whatever you do Jess, just don’t give up hope, but if you do call me. I’m sure with your bankroll the missus wouldn’t mind you being part of the harem.

Your pal,

Phineas G.

* By tasteful I of course mean stopping short of embarrassing Larry Flint and employing the use of animals or midgets as props. I would however suggest utilizing copious amounts of pudding, whipped cream and perhaps a couple of friends who start out dressed as naughty cheerleaders.

** Apologies to Agent Bedhead for stealing the unsolicited letter of advice bit. Perhaps she won’t lock me in the basement, for more than a week, this time.



4 comments

I’m convinced that poor Jessica is never going to have a real man in her life, let alone marry one. Any guy who marries her has to implicitly (or maybe even explicitly) agree to obey daddy and let him totally control the relationship. He might even videotape it all!

And no, you’re not grounded, but could you sweep the pool tomorrow for me? Thanks, dahling. :mrgreen:

09.13.06 | 4:24 pm
ktel60

Poor Jessica, so envious of her more-successful sibs Bart, Lisa, and even Maggie

09.13.06 | 7:20 pm

I sit down to pee.

Well, that’s not strictly accurate. It’s more like, when I realize I have to pee, I don’t bother getting up.

09.14.06 | 1:24 pm

:shock: Dude, you’re so never going to live that down.

09.14.06 | 2:14 pm


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