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.

Photos: Splash News

  1. angeleyes


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

  2. Que

    Que sappy.

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

  4. jerry mcgregor

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

  5. Jake

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

  6. gross

    those earrings are foul

  7. Ang

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

  8. E

    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

  9. Nice...

    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

  10. kally34

    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 !!!

  11. she looks so pretty and squishy. real squishy.

  12. JJ

    a completely unfitted dress should stop all that fat talk…

    riiiight good choice Jess

  13. Jrz

    Hey, kally34, I heard there’s an interesting place if you want to find some punches to the fucking face….it’s called 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?

  14. Quinn

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

  15. ReRun

    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!

  16. steve

    “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.

  17. John Madden

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

  18. SaraS


    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

  19. oops

    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…

  20. sigh

    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.

  21. Lowlands

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

  22. Mia

    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.

  23. Farmer Ted

    Two words.

    Jerking now.

  24. Deacon Jones

    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.

  25. Goddess mimi

    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!

  26. Matt

    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?”).

  27. nipolian

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

  28. __

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

  29. FFFFffffffffaaaaaaarrrrrrrrrrt

    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.

  30. 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):

  31. ___


  32. Rick

    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.

  33. Photoshop Police

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

  34. havoc

    I’m sorry, but she just looks stupid.

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



  35. A woman's anus is a man's best friend

    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

  36. Andrea

    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.

  37. sally strutters

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

    @ 30 — LMAO, that shit was hilarious!

  38. Mark B


    Andrea, you say that like its a bad thing…

  39. Andrea

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

  40. ___

    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.

  41. I hate you

    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.

  42. netstarman

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

  43. duh

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

  44. netstarman

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

  45. kevin

    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.

  46. sin

    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.

  47. S

    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!!!

  48. Delgo

    I <3 veiny breasts.

  49. Biology Major

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

  50. S

    lol or maybe she just has really big tits?

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