Jessica Simpson has had her share of ups and downs in Cabo from her breakup trip with John Mayer to a romantic vacation with Tony Romo and her family to dateless birthday times. As for this most recent jaunt south, we're not sure if it's to get away from ending things with Tony or just a moment away before getting back to him, but it looks like she's having fun on her trip already. She was spotted busting a move and toting around her black MacBook in the sun. Even Daisy got in on the lounge chair action. While I'm always rooting for Jessica to find love, at least she's comfortable in her skin again — hopefully that is boyfriend or not.
Isabella Oliver
Rocha.John Rocha
Tory Burch
sadly shes not confortable in her own skin
1thats nice.
2do you think that they have a place down there or do they stay at a hotel each time? it's like they are ALWAYS in cabo....
i hope that things work out for her. i don't know if i really like jess for tony but if they were happy...and it was the dad that got in the way, maybe he'll learn to lay off a bit.
3she looks gorgeous
4It looks like she's having a good time.
5I think they have a vacation home over there. Must be nice!!!!
6Who would have thunk Jessica would be eclipsed by Asslee?
7i've always liked her, they seems to have a vacation home there or know someone there.
8Yeah, I was wondering the same thing about them always visiting Cabo. I sure hope she enjoys herself and doesn't waste the lovely surroundings and takes time to just relax.
9I don't think she's comfortable in her own skin either.
10Rough life! Geez.
11Zahara Pitt - word on that. Looks like she's having a good time? It looks to me like she's aware of the cameras.
"always rooting for Jessica to find love"? The sad thing is that she had it. She had love and she and her fame/money hungry father threw it away for what they (at least her father) thought would be greener grass. Can't be comfortable in your own skin if someone else is dictating how you should live in it.
12They probably stay at One and Only Palmilla. It's a HUGE resort community. With hotel rooms and houses to rent.My picture icon was actually taken there.
13Maybe with her Sis getting married, and the same wedding planner from her wedding planning it, she needed sometime to find her ground. Celebs have it tough when it comes to their love life when everyone (family and fans) try to decide what is best for them. Enjoy your summer Jess, you deserve to be happy
14It looks like she can see the photographer. She's made her own decisions and what ever happened , it's her responsibility. She makes poor choices and is too needy. Considering that she's 27, she's not too mature.
15does she have a laptop in that first pic? checking email from tony on vacation much????
16I doubt she is seriously distraught or anything... not like its her first breakup
It is almost June, I'm ready for my Vacay!
17She has made her own decisions and yet, people are always feeling sorry for her. Why? People get together and break up. If she will not break free of her creepy father, she will NEVER find anyone. I liked her with Nick at first and then after a few episodes, I couldn't understand how anyone could live with that spoiled brat. He was a freaking saint to put up with her diva like behavior for so long. Ugh, she annoys me. I think if they actually broke up, she will be devastated. I think she had a lot riding on this one. QB of her home state. He is actually cute and seems normal and non controlling unlike John Mayer, but when she started talking marriage and babies, maybe he freaked. He wouldn't be the first guy to do it, nor the last. I hope she decides to stay in Cabo FOREVER!!
18my sentiments exactly blob
19It looks like it could be the same place she was photographed at before, so either she has a place down there or always stays at the same place.
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