Jessica Simpson & Tony Romo do Valentine’s Day

February 16th, 2009 // 87 Comments

Still together, Jessica Simpson and Tony Romo went out in New York City for Valentine’s Day, and she’s gotta be pregnant. Otherwise, I don’t know how else to explain her outfit. Not counting she’s Jessica Simpson and thinks “Maternity” means medium in French-talk.

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Comments (87)

  1. angeleyes | February 16, 2009 at 12:35 pm

    FIRST!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

    She is so overated. I don’t see what he sees in her. The only thing worse than a blonde is a fake blonde.

    Reply
  2. Que | February 16, 2009 at 12:36 pm

    Que sappy.

    Reply
  3. mztry | February 16, 2009 at 12:36 pm

    How many of us have gained weight while in love and lost weight while recuperating from heartache?

    Reply
  4. jerry mcgregor | February 16, 2009 at 12:39 pm

    OMG those breasts! im hungry for some milk now……

    Reply
  5. Jake | February 16, 2009 at 12:40 pm

    If she continues on this path, she’ll be wearing black trash bags by Friday. (yes, bootlips, I said “black trash”, let it go…)

    Reply
  6. gross | February 16, 2009 at 12:41 pm

    those earrings are foul

    Reply
  7. Ang | February 16, 2009 at 12:44 pm

    Nice front-butt. I bet when she caught her reflection she got confused and started turning around and around.

    Reply
  8. E | February 16, 2009 at 12:54 pm

    why does she keep wearing these unflattering outfits?? She clearly doesn’t know how to dress her body when she’s at a heavier weight

    Reply
  9. Nice... | February 16, 2009 at 12:55 pm

    Dear Great Britain and Fucking France:

    Thanks for almost taking out the entire earth.

    LONDON – Nuclear-armed submarines from Britain and France collided deep under the Atlantic Ocean earlier this month, causing damage to both vessels but releasing no radioactivity, a British official said Monday

    Reply
  10. kally34 | February 16, 2009 at 12:55 pm

    I heard that there is an inter esting place for all h O t g irls and guys,
    seems it is named: ___T allmingle Co M___ ,if u want to find some fun or lov ers, please have a try !!!

    Reply
  11. http://www.popduds.com (now open) | February 16, 2009 at 12:56 pm

    she looks so pretty and squishy. real squishy.

    Reply
  12. JJ | February 16, 2009 at 12:57 pm

    a completely unfitted dress should stop all that fat talk…

    riiiight good choice Jess

    Reply
  13. Jrz | February 16, 2009 at 1:01 pm

    Hey, kally34, I heard there’s an interesting place if you want to find some punches to the fucking face….it’s called punchkally34inthefuckingface.com. You can meet a bunch of people who’d like to Chris Brown your stupid spamming ass! It’s a real hoot! Please have a try.

    Anyway, what do you think he does with them big earrings?

    Reply
  14. Quinn | February 16, 2009 at 1:02 pm

    She looks awful and WhyTF choose the ugliest dress possible….

    Reply
  15. ReRun | February 16, 2009 at 1:05 pm

    Oh yea…she’s preggo alright. You can see it in his face. Life WAS looking pretty good for Romo. Its over now and he knows it!

    Reply
  16. steve | February 16, 2009 at 1:05 pm

    “why does she keep wearing these unflattering outfits?”

    It’s almost as if she’s become fat, and doesn’t look as good as she used to regardless of what she wears.

    Reply
  17. John Madden | February 16, 2009 at 1:07 pm

    Romo is being very supportive of Jessica, but mostly because now her butt looks almost exactly the same as Jason Whitten’s.

    Reply
  18. SaraS | February 16, 2009 at 1:10 pm

    Steve-

    there are more flattering ways to dress her body type, its not like she’s freakin Rosie O or something

    she could definitely wear stuff that was more slimming and less sloppy looking

    Reply
  19. oops | February 16, 2009 at 1:11 pm

    Does anybody edit news headlines anymore? Just saw this one, about the Buffalo plane crash: “Crash victim: ‘Everybody loved being around her’” Wonderful, I think they recovered about 47 small pieces of her…

    Reply
  20. sigh | February 16, 2009 at 1:17 pm

    wow… even her tatas and skin are getting busted looking. booo. too much make-up! i hope she is preggers, otherwise she just aged really fast.

    Reply
  21. Lowlands | February 16, 2009 at 1:18 pm

    She looks great and i bet she bangs like a locomotive! Any (free) sextape available?

    Reply
  22. Mia | February 16, 2009 at 1:21 pm

    I suspect Jessica buys clothes based on these 2 criterias:

    It must be an expensive designer label.
    It must fit.

    This is why Jessica looks dumpy lately because she is short, overweight, and does not know how to buy clothes to flatter her weight gain.

    Reply
  23. Farmer Ted | February 16, 2009 at 1:23 pm

    Two words.

    Jerking now.

    Reply
  24. Deacon Jones | February 16, 2009 at 1:23 pm

    Wow…Romo looks thrilled to be spending time with her.

    Yes Romo, you have to deal with this train wreck the other 23 hours and 45 minutes out of the day when you’re not titty fucking her.

    Reply
  25. Goddess mimi | February 16, 2009 at 1:28 pm

    19
    This is not the place for that kind of news. We are trying to have fun here don’t you get it? And why is it that every time some idiot dies they are alway “the nicest friend ever, the sweetest this or that”? SHUT UP already she’s dead!

    Reply
  26. Matt | February 16, 2009 at 1:31 pm

    Whatever “the magic touch” is, Tony Romo has the antidote. Latent homosexuals don’t seem to be doing all that well these days (“Hey–YIKES–umm, sorry, Mr. Cruise, I didn’t know you were in this restroom…yes, of course, you were drinking a latte, what else could that be?”).

    Reply
  27. nipolian | February 16, 2009 at 1:32 pm

    If you look at the 8th pic, you can see her actually morphing into Tammy Fay Baker right in front of the camera……..creepy.

    Reply
  28. __ | February 16, 2009 at 1:33 pm

    Hey MIA,
    “Criterias” is not a word. Stop trying to sound smart.

    Reply
  29. FFFFffffffffaaaaaaarrrrrrrrrrt | February 16, 2009 at 1:35 pm

    Why did this short squat cow-to-be let the world know she passes gas? Tony is so very lucky! I wonder what he see’s in her? I don’t get it. Particularly John Mayer who is very bright. I have a feeling being with her is like hanging out with your dog all day.

    Reply
  30. todders | February 16, 2009 at 1:39 pm

    Mmmm. More meat = mor boobage…

    I am all for Jessica eating seconds…

    yo, check out this hilarious video I saw about the Girls Gone Wild Porno Bailout (watch out for the dude in the stache):

    http://blog.digitalfuntown.com/dft-blog/2009/2/6/larry-flints-porno-bailout.html

    Reply
  31. ___ | February 16, 2009 at 1:40 pm

    DO NOT CLICK ON THE LINK @ #30. THIS WILL INFECT YOUR COMPUTER WITH A VIRUS!!!!!!

    Reply
  32. Rick | February 16, 2009 at 1:41 pm

    She’s made her “new curvy figure!” (fat) into a huge deal and the snacking class is eating it up (“real women have curves!”), but the truth is she’s weak and dependent, so she reflects the man she’s with. Romo is a slob, just look at him. That’s fine for football, especially since he plays a skill position that doesn’t require perfect conditioning. But she mimics his lifestyle (have sex, pig out, watch TV, have sex, pig out…) and then wonders why people say she let herself go when she waddles on stage or out for the paps. Yes, girls, she’s an icon for the independent woman.

    Reply
  33. Photoshop Police | February 16, 2009 at 1:45 pm

    I’ve been saying she’s pregnant for WEEKS now!
    Someone confirm it with them already?

    Reply
  34. havoc | February 16, 2009 at 1:46 pm

    I’m sorry, but she just looks stupid.

    The boobs look fun…but that face. Duuuuuuh…..

    LMAO!

    .

    Reply
  35. A woman's anus is a man's best friend | February 16, 2009 at 1:50 pm

    Tony should have stuck to ass fucking this pig. Now he will get to know her for the next 19 years ha ha ha ha ha ha

    Reply
  36. Andrea | February 16, 2009 at 1:57 pm

    He looks like the type of guy who makes the girl ride on top, doing all the work, and when he gets up you see a skid mark on the sheets where he was lying.

    Reply
  37. sally strutters | February 16, 2009 at 2:05 pm

    @ 31 — What r u talking about? n00b!!!

    @ 30 — LMAO, that shit was hilarious!

    Reply
  38. Mark B | February 16, 2009 at 2:10 pm

    @36

    Andrea, you say that like its a bad thing…

    Reply
  39. Andrea | February 16, 2009 at 2:13 pm

    #38 – if I want bean dip in bed, I’ll get it from the refrigerator.

    Reply
  40. ___ | February 16, 2009 at 2:14 pm

    #37,
    I don’t know, I was just repeating what someone else said after he sent that same link last week. I didn’t click on it but was just trying to do the right thing. Better safe than sorry. Click at your own risk.

    Reply
  41. I hate you | February 16, 2009 at 2:33 pm

    I think it’s kinda hot when a chick gains some weight and still keeps her sweet tits. Back in the day, the skinnier you were, the less attractive you were considered. Don’t get me wrong, a chick that was born fat and has all the fat-chick qualities is not attractive to me, but a chick that is “healthy” or a bit thick that fluctuates in weight is hot to me. I am NOT a chubby chaser by any means, I just hate these Kate Moss/Sienna Miller stick figures that have nothing to offer.

    Reply
  42. netstarman | February 16, 2009 at 2:37 pm

    Did Tony Romo at least warn the chefs that Jessica was in the restaurant ? Or at least order half-portions for her.

    Reply
  43. duh | February 16, 2009 at 2:38 pm

    Jessica Simpson was never a Moss/Miller stick figure. She was always curvy. Now she’s lumpy.

    Reply
  44. netstarman | February 16, 2009 at 2:39 pm

    Well black is slimming , maybe paint some white on the front of that outfit and we can call her Orca whale .

    Reply
  45. kevin | February 16, 2009 at 2:50 pm

    Romo got to be the dumbest man in the world to let this ho trap him. Now she is going to be a big fat pregnant pig. She will eat like a pig for 9 month.

    Reply
  46. sin | February 16, 2009 at 2:54 pm

    His Valentine present to her dripped out of her mouth and onto those NICE tits.
    Have a nice off season and fuck that thing every way possible. when training camp comes, drop her like T.O. drops a pass. She is only good for sex. Her daddy knows that.

    Reply
  47. S | February 16, 2009 at 3:27 pm

    Oh I feel like for some reason, after all this depressing shit about the economy, Jessica and Her freak of a father got together and said: People want to get their minds off the horrid downfall of the economy how can we profit off this? Oh I know! Jessica go eat your sisters new kid!

    Thus why she is getting more publicity now then she was several weeks before! Mad geniuses!!!

    Reply
  48. Delgo | February 16, 2009 at 3:37 pm

    I <3 veiny breasts.

    Reply
  49. Biology Major | February 16, 2009 at 3:39 pm

    Pic #6…giant blue veins becoming visible in the breasts…a common occurence in early stage pregnancy…just sayin’

    Reply
  50. S | February 16, 2009 at 3:44 pm

    lol or maybe she just has really big tits?

    Reply

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