As Ashlee Simpson's baby bump grows bigger, her sister Jessica is putting in practice for her upcoming duties as an aunt. Yesterday she was back from her time in the Midwest with Tony and his parents, out to lunch in LA with friends like Ken Paves and spending some more quality time with her adorable godson. Her new album is getting even more praise from the country music world lately, but it looks like she could always find a side gig as a babysitter for her baby sister when the time comes.

















Emporio Armani
Timberland
Karen Millen
What is this? A competition on who wears the ugliest dress?
1That poor kid.
2what a cute baby she is beautiful
3cute baby
4whatever I love that dress!
Ken, looking a little rough babe
5Ken Paves is so creepy looking.
6If I were Ashlee I wouldn't be so quick to let Jessica babysit.
7How do these women wear these dresses and not trip and fall?
8Short women should not wear long dresses!
9Is it just me or does it seem like she holding that baby up to the camera trying to send Tony subliminal messages?
"Tony..you will make babies with me! Tony...I'll be a wonderful wife and mother! Tony...You will be the father of my children"
Papa Joe is probably somewhere with a Tony Romo voodoo doll trying stimulate his vas deferens
10First Brit and now this? Gosh, two of my fave hate targets first thing in the morning. Thanks Pop!
This screams to me "Hey everybody! Don't I look so cute and good with a baby? Now go and tell Tony that it makes perfect sense to marry me and get me pregnant!"
11That kid doesn't look too thrilled to be held by her
12Why is it that in every picture of Jessica with this baby (past and present) she is holding it facing outwards. It kinda seems like she's toteing him around for attention.
13
Jaxon!!!
14Don't just stand there Ken, fix Jessica's roots!
15Jax - I love u
Joe probably bought that baby for the purpose of her holding it to the cameras. Then it goes back in its cage.
16
jaxon!!!!
17Um.. is it just me or does her sunglasses look weird on her face?
18I'm not being mean, I'm just wondering if it's just me. :|
awww, these pics are adorable!! i love jess, she's going to be a GREAT aunt!
19sweet, she was in wisconsin! we don't get much celebrity action round here. haha
20Ken looks like he's on drugs...
Jessica always seems to hold babies this way...does she not know how to hold a child??? Wierd and awkward.
21Back to the cage
Kinda like the lion tamer at the circus but instead of roaring on command the baby smiles, coos, and says "mommy"
22LOL, jax. you beat me to it.
Indigo4320 - she holds babies that way so she can advertise it like how she holds her purses a certain way so that the photogs are sure to get good pics of it.
23be nice, lmfao jaxon
24well at least we know that she doesn't shy away from kids. i have to say though that it isn't her best picture. she looks a bit older there. oh well...could have been the light.
25who does that po'baby belong to?
26
27Poor baby looks uncomfortable. Someone should be spanked for allowing that nitwit around their baby.
28Those roots are a NO NO..Ken, How can you let your best customer and walking ad go out like that?
29mustache?
30I don't like holding a baby like that...she must be scared to get drool and puke in her hair
31hahah jaxon
32Ken needs a haircut...and why is Jess holding the baby toward the papparazzi?? I'm sure he doesn't want a million flashbulbs in his face. They all do look cute though!!
33Could that baby look any more miserable???
34awwwwwwwwwww how cute
35lol! CHOPA! Campesina! lol
36Those two were hopefully on their way to the salon after lunch. Jess' roots are ridiculous and Ken's hair is getting a little out of control.
37wow, I'm sure the baby would look happier if she wasn't holding him so awkwardly, (For the camera, of course...
) I probably shouldn't complain too much though, at least
she's holding him right side up.
38Her boobs look saggy!
39She's holidng the baby all prissy.
40lol - Brian and Jaxon
That baby is adorable.
41Nick and Jessica LOL
42It's not a niece or nephew Jess wants. I'm sure at this point she wants her OWN.
43Many Pediatricians believe that babies should be hold face forward so they could observe the surrounding. So Jessica is very wise to hold the baby that way. As for the pictures shown the baby ids not happy, you should be to if there are many camera flashs blinding you.
44Cute baby
45why is it that she can NOT hold a child correctly. he looks so uncomfortable.
46The baby is cute. but it seems he is not very comfortable.
47how paris hilton of her to hold a baby like that while paps are around. ugh, its one thing to wh*re out your own kid...dont do it with someone else's kid.
48Hopefully dressing like that doesn't come with the auntie package. Although I do like her shades
49I will say that when my friends baby needed to go number 2, we hold her like that
50she still looks very uncomfortable
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