Wed, 20 February 2008 at 1:26 pm

Jessica & Ashlee Double Date

Singing sisters Jessica and Ashlee Simpson enjoy a pre-Valentine’s Day dinner at the Grand Lux restaurant at the Galleria Mall in Dallas, TX with their boyfriends — footballer Tony Romo and rocker Pete Wentz, repsectively.

“I think they’re going to get married,” Romo’s pal Michael Starr tells US Weekly.

“They’re perfect for each other,” another pal adds. “They’re both funny and wonderful and kind. I’m rooting for them.”

Photos: Tara Tilton/Us Weekly
Posted to: Ashlee Simpson, Jessica Simpson, Pete Wentz, Tony Romo
Related posts:

JJ Links Around The Web

Gwyneth Paltrow talks Morocco - LaineyGossip
Anne Hathaway and her BF get in a minor accident - PopEater
Ashlee Simpson and Bronx head to the mall - PopSugar
Elin Nordegren talks to a divorce lawyer - Dlisted
Miley Cyrus shops in Dublin - JustJaredJr
Courtney Love lashes out on Facebook - TheSuperficial
Check out Kristen Stewart as Joan Jett- Celebuzz

Pascal Le Segretain/Getty

51 Comments

Pages: « 1 [2] 3 » Show All

# 26

bejeebus @ 02/20/2008 at 4:29 pm

natalie,
you speak the TRUTH, girl!

@reply | Flag This

# 27

tas @ 02/20/2008 at 5:02 pm

It seems to me like Jess has found someone who interestingly has alot in common with her ex- Nick. Sports lover, down to earth, mans man, and Tony and Nick even look alike (although Nick is better looking). I’m sure Tony pampers her and puts up with her dumb behavior like Nick did too. As for marriage, I don’t see it lasting. I don’t think Jessica has grown up enough, or is selfless enough to be in a marriage. She is also still tied to the apron strings of her father, which is trouble in and of itself. Tony will tire of that real fast. Its way too soon for them to even be considering it, and all the gossip about it may damage their relationship. I don’t give it a year even.

@reply | Flag This

# 28

David @ 02/20/2008 at 5:12 pm

This date is such a set up and Tony must be the dumbest man alive.
The friend leaking the marriage thing is to push Tony in that direction. The Simpsons are so phony and sure can’t sing. Her dad went out and found a man with the most money he can find to pull this family out ruin. I have no respect for someone as dumb as Tony.

@reply | Flag This

# 29

Mary @ 02/20/2008 at 5:24 pm

Jessica side is sure pushing this all the way to the alter. I see they are far more desperate than ever. How can he sit their and be so stupid at least John Mayer was smart enough to run when she started pushing him to the alter. I remember when she started the gossip about rings when she was with John. Any man could be sitting in that spot long as the dollar bills add up right for Papa. I feel like she is being sold for the highest bid.

@reply | Flag This

# 30

Buttercup @ 02/20/2008 at 5:29 pm

Jared, did you spell “respectively”, “repsectively” because that’s how Jessica would spell it? ;)

@reply | Flag This

# 31

OMG WAH? @ 02/20/2008 at 5:40 pm

RUN ROMO RUNNN !!!!!!!

@reply | Flag This

# 32

lj @ 02/20/2008 at 6:02 pm

I agree with# 20, 25, 27, and 28. Jessica is more desperate every day. This photo looks like a set up. What kind of brilliant conversation did they have? I heard that Tony’s had a crush on Jessica for a while. If he watched Newlyweds he should have seen what she’s really like, a shallow . self absorbed, moron who really didn’t make an effort for her marriage to work. Considering she didn’t have sex or live with Nick before hand, you think that she would try to make an impression instead of being a lazy slob. It seems like they deserve each other.

@reply | Flag This

# 33

JANE @ 02/20/2008 at 6:26 pm

HAV 2 AGREE WITH NATALIE……RUN….TONY…RUN…..GET AWAY…..

@reply | Flag This

# 34

MovieMadness @ 02/20/2008 at 6:31 pm

“cough” haters “cough”

@reply | Flag This

# 35

her @ 02/20/2008 at 6:57 pm

Honestly….I kinda hate Ashlee….she doesn’t deserve Pete.

@reply | Flag This

# 36

Kym @ 02/20/2008 at 7:21 pm

Tony isnt dumb. By July, when training camp starts for football, Jessica will be long gone. I give this little “romance” at most, 4-5 more months. It probaly won’t even go that far anyways, but 4 sure Jessica will be dumped by July.

@reply | Flag This

# 37

JT @ 02/20/2008 at 7:44 pm

Jessica and Tony are cute together. I hope they can make it work.

@reply | Flag This

# 38

Teresa @ 02/20/2008 at 7:47 pm

I’m sure Tony knows Jessica a lot better than any of you guys do. He’s a big boy, he can make his own decisions and if he’s happy with her, so be it. Don’t get your panties in a twist when you know nothing of either of them personally.

@reply | Flag This

# 39

colleen @ 02/20/2008 at 8:55 pm

Completely agree with erin, last time the no pre-nup backfired. This marriage will make up for the loss.

@reply | Flag This

# 40

Troy 61 @ 02/20/2008 at 8:58 pm

Tony, Why buy the cow?

@reply | Flag This

# 41

How this went down @ 02/20/2008 at 9:38 pm

And then Michael Starr was handed a twenty from papa joe, that, or a promise of a bj by Jess.

@reply | Flag This

# 42

bill @ 02/20/2008 at 9:51 pm

I agree with thats how it went down. I hope Starr got paid well. The Simpson clan can only keep Tony busy and distracted for so long. I’m sure they hope to have them married by the time he opens his eyes.

@reply | Flag This

# 43

luv vanessa @ 02/20/2008 at 10:12 pm

lol! that’s just so cute… and hilarious!

@reply | Flag This

# 44

sweet kisses @ 02/20/2008 at 11:32 pm

Heres a simple thought. Tony doesnt want to run. Have you guys ever stopped to consider your perception of Jessica may be wrong and she really is a sweet and kind person that Tony enjoys being with? What a thought, eh?

@reply | Flag This

# 45

Sara @ 02/20/2008 at 11:36 pm

I feel sorry for her these two sisters and their dad want to be in hollywood so bad and none of them have talent.
You can feel the desperation coming from them. Well TR you get what you get. Lots of men watch the show lusting after her but soon understood what she was all about. Hell figure it out by then she will have her hands on some of that money.

@reply | Flag This

# 46

Jude @ 02/21/2008 at 12:16 am

I saw them at the Galleria in Dallas. I was like “wheres papa joe?”

@reply | Flag This

# 47

Iced @ 02/21/2008 at 12:41 am

Ugh..this stupid Bit*h didn’t hang around Dallas so much before she got with Tony..now he brings her stupid a*s here all the time. Thanks Tony!!! I can’t wait for his time to be up in and Dallas so he can go somewhere else and take this uneducated moron with him!
Tony’s a joke!

@reply | Flag This

# 48

Taylor @ 02/21/2008 at 12:53 am

Run, Pete, RUN!

I dislike Ashlee greatly.
But I don’t find Jessica that horrid anymore…
She seems less “hoe-y”

Run, Tony, Run?
I don’t know.
But I sure as heck wouldn’t marry her myself.

@reply | Flag This

# 49

KimB @ 02/21/2008 at 5:04 pm

whats with the toothbrushes on the table?

@reply | Flag This

# 50