Jess, looking every bit the scallywag in her school boy hat (yes, I just wanted an excuse to use that word), dined with her beau John at the Ivy at the Shore yesterday. The two recently returned from their vacation in Rome, but it looks like they didn't leave the romance in Italy. Awwww. Speaking of Jess and her love of gorgeous places, girlfriend says she's looking to release a book of photography. Sounds. Brilliant. Meanwhile, I love me some Jess and John (obviously, and probably to a fault), but I don't love me his chin hair. Let's keep the flowing locks on top of our heads, guys.
To see more of John and Jess and then some of just Jess doing Jess stuff...like shopping just read more

















Luella
Tara Matthews
sweatyBetty
I dont' hate them. I love that she's happy. and i like him a lot. I'm going to one of his concerts here in July. But WHY won't anyone take a shot of him LOOKING at HER???
1Ok well a shot of him looking at her like he likes her company and not just bored.
2She's looked really good lately.
3He, on the other hand, looks horrid.
Why John, why do you keep punishing me? I thought you were smarter
4smarter than a booty call
5I got to admit it, I'm starting to really like them as a couple.
Style Before Comfort!
6Deba he'll hear your call....one day. LOL you're so funny.
7asarwan, because he is not into her and he doesnt want to be rude with her and hurt his feelings, but one day he is gonna say you are way to stupid and broing for my taste.
Crossing my fingers!!!!!!!!!!
8That hat is so Britney Spears circa 2001 lol
9sorry hurt her feelings
10why can't ya'll just accept that maybe, just maybe there's more to her than we saw on newlyweds?
11I love them together!!! I think they both look hot here
12I accept it ask4. hahahaha
13I love love love her. Even if shes not with nick.
They both care ALOT about what people think of them....and it's annoying to watch them ACT like they don't.
Their WHOLE WORLDS are built around selling their "craft" to adoring fans.
So Jess REALLY needs to SNAP OUT OF IT and go back to being herself and John needs to kinda commit to who he wants to be;)
14Deba I knew what you meant.
I know there's more to her than just the newlyweds. I dotn' think she's an airhead by any means. Nor do i believe she's a rocket scientist. But these two make me feel like i'm crazy. I feel like i'm waiting for that second when they'll look at the cameras and go! HA HA GOTCHA!
It's probably rough on her with seeing Nick and Vanessa. And it's easier sometimes to deal when you have someone else to focus on. Who knows. i wish i knew if it was a joke or not.
15i think she looks great!
16I doubt than in her is more than "Newlyweds". The reason why Im so againt this relationship its because I think John is aagreat musician and really talented, and by association with Jessica all he gets to be is "Jessica's boyfriend". He doesnt really shine on his own. Plus its Jessica!!!!!!!!! Do I need to say more?????
17I think they look cute here. She looks a lot better why she's dressed casually like this.
18It's only been several months....John has to come to his senses eventually. He just seems so educated and cultured and she dropped out of school and didn't know buffalo wings were chicken.
19Come on, Molly! Where are the Krasinski pics you promised!!!
John's been reminding me a little of Edward Scissorhands lately.
20Dude, I still think Jessica Simpson looks like a drag queen with that brown hair.
21they are boring and she looks so ordinary with brown hair. It does nothing for her but make her blend in the crowd, and she does not have enough going for her talent wise to be able to blend in, in other words, her sex kitten look is really all she has going.
22lol @ unabellasorpresa... I never really found whay guys find so soo hot on her... hot is Scarlet, or Halle, or Angelina not Jessica!
23john has always reminded me of edward scissorhands!
24So, so true mar. She just doesn't have any talent and has gotten by with her (amazing) body and I guess, looks. Which is why I wonder what these two talk about over dinner at night.....
25I remember when I listen to his first song "Your body is wonderland", I love that song! And immediately went to buy his CD and thought hey! this guy is talented and his music makes sense... John please get your grip!
26I remember when I listened to his first song "Your body is wonderland", I love that song! And immediately went to buy his CD and thought hey! this guy is talented and his music makes sense... John please get your grip!
27Yay...I'm glad someone else also sees the resemblance to Edward.
28i cannot wait for a knock down drag out screaming match between these too, i think that would be the only thing that would make them the least bit interesting. im really very happy that jessica has decided to publish a book of photography. isnt that what every out of work musician does?TEAM FLUTTER!!!!!
29I'm sticking with my theory John just wanted sex with the bimbo but she got to manipulate him into a relationship (Apparently the chick is not that stupid)
30I think her boobs must have secret powers. I gave him more credit than that.
31I think you nailed it, Deba. No pun intended
32hahaha
33Am I the only one that think she looks a lot like Ash when she had the dark hair going on? The resemblance is actually quite scary in the bottom row pictures!
34I thinks he's just a guy anyway talented or not just a guy, perhaps he enjoys teaching her I don't know. But for me she always looks like soooo into him follow him everywhere, a mean she practically does not have a life she just living his life, his tour.....and matching her hair to his hair! She doesn't have personality at all!
35I think once Jess realizes that John isn't going to take care of her, she's going to drop him. Jessica needs a nanny, not a boyfriend.
36Maybe he really likes her.
37Since he is such a talented musician that is so smart I don't think he would do this as a joke. He doesn't need the publicity.
I like his stubble! Let the man be...
38Jessica was much cuter in her Newlywed days. Now she looks harsh and I don't like the hair color. Makes her look manly.
39They look cute. And what's that a smile? Ok, not a smile, a smirk, ok not a smirk, a slightly but not completely upturn of the corners of John's mouth!
40These two have totally grown on me. I love seeing them together ♥
41This is popsugar.com, not Time Magazine. I mean, I like proper grammar as much as the next person, but this is gossip. It's to spice it up a bit.
42I'm all for comfort over style, but when did she start wearing hoodies and sweatshirts 24/7? She wasn't like that BEFORE she met him...she needs to be herself, instead of changing her style for whoever she happens to be with.
43I think Jessica looks great....and I love the handbag!!!! I want it...!! I wish they would give their castaways handbags to the fans
44i love them together..i love john mayer and he's deffinatly a step up from nick!
45I really love Jessica and I think she looks better than ever. John always looks sickly and has a HUGE head. I don't understand this odd couple. I also sort of depsise John for lying about their relationship early on.
46JESSICA looks great! Love her. You can keep posting these pics.
47Love her hat
48Love her bag
Love her sunglasses
Love her casual but not frumpy look
LOVE LOVE LOVE HER!
I still love her dark hair. It's so gorgeous.
49i love them together and jess seems to have changed and has an air about her she didnt have before, whatever it is keep it up!!! we love u!
50Post New Comment
Please share your opinion with our community, but make sure it is on topic and follows our Community Rules. We moderate comments and prohibit personal attacks, threats, spam, lewd images, or the promotion of your personal website.