Jessica Simpson's BFF CaCee Cobb: "She's Found Happiness with Herself"

The new mom's closest pal explains why she's loving life now more than ever -- and shares some funny secrets from her past!

She has an adorable baby, a handsome fiance -- and she's on her way to having a brand-new body. So it's no wonder that Jessica Simpson often has a smile on her face. "She’s just in the happiest place I’ve ever seen her in," her best friend CaCee Cobb tells iVillage. "Even on her worst day, she’s still happy with her life."

Cobb admits that the new mom to 4-month-old daughter Maxwell (with fiance Eric Johnson) has come a long way since they first became friends 13 years ago. And while the Fashion Star mentor (who's also the new Weight Watchers spokesperson) has fully converted to "responsible" mom, Cobb can still remember a time when she thought of Jess as the "dirtiest girl" she'd ever met!

Read on to find out how Jessica is encouraging CaCee to lose weight, why her fiance Johnson is like "Superdad," and why CaCee thought Jess was joking when she first told her they were engaged.

How did you and Jessica meet?
It was back in ’97, I guess. I worked in the A&R department [at Columbia Records], and I worked on all of Jessica’s records. We had a very different type of relationship at first. We would talk on the phone all the time -- work-wise. When she started to go on tour they were looking for a road manager, and they offered me the job. I was like, "Sure, but is that gonna be weird? We don’t really know each other." And the crazy thing is that the first day out on the road with her, something happened with our travel and it screwed up. I didn’t have a hotel room, so we had to sleep in the same room in the same bed. The first day we even traveled together!

That's one way to get to know each other!
Yeah, we sat up all night. It was like a slumber party. We just hit it off immediately, and we’ve been literally best friends since '99 I guess.

What do you think it is that makes Jessica such a good friend?
She's one of those people that whenever you’re going through something she will totally take it on. As if she’s right there in it with you. I mean, it’s gotta suck on her end because she’s totally investing every bit of her time and energy into someone else’s problems. And she’s always there for me. I’ve showed up at her house at night saying, "I’m spending the night!" No matter what’s going on in her life, she always makes time.

She’s known publicly for being this goofy, fun girl who doesn't take herself too seriously...
Oh, yeah! She’s a dork. But I’m a dork, too. And I think that’s probably the reason we are so close. She never takes herself too seriously, and I love that about her. Going through everything she’s been through and owning a billion-dollar empire...It’s just insane because she’s still the exact same person she was when I met her.

Are there any goofy moments you've had with her that stand out?
I always tease her because I’m very OCD and very organized and clean. [She used to come stay with me in Dallas] and she would just totally ransack the whole apartment. She used to wear contacts, and I remember watching her one time sitting in my bed and taking her contacts out -- and she’s throwing them on my floor! I asked her, "Why do you throw your contacts on the floor? That’s so rude." And she was like, "Oh no, they dissolve. Don’t worry about it!" And I will always remember thinking, "This girl is the dirtiest girl that I’ve ever met."

Now Jessica is engaged to Eric. Do you remember the first time she told you about him?
I don’t remember exactly, but I do remember thinking, "Okay, you met this guy." And I really didn’t think anything of it. And then the next thing I knew, it was her birthday and we were all going to Italy together. I was like, "Okay, well this might be pretty serious!" But I liked the fact that I didn’t know anything about him because in the past she’s had relationships with people who were in the public eye -- and not to say that they’re not great guys, but Eric is just so amazing! It’s really great to see her with a guy who's just really down to earth, very humble, very smart and literally adores her. I couldn’t imagine her having a baby with anyone else in this world. Honestly, he’s the best thing that’s ever happened to her.

How did you react when she told you they were engaged?
Well, she called me, and she had me on Bluetooth, and I didn’t even realize it. She was like, "Okay, are you ready for this? I’m engaged!" I sat up and said, "Shut up! Are you serious?" I thought she was joking 'cause it happened really quick. But then she was like, "Yeah! We’re both here in the car!’ I was like, "Oh! Heeeey!" Ten minutes later I was geeked out of my mind driving my car over to her house to celebrate with them. It was amazing.

You're the godmother to Jessica's 4-month-old daughter Maxwell. What's Jessica like as a mom?
It’s almost like she’s a different person. When she got pregnant I was like, "Oh God. This is going to be interesting!" She’s so great. I remember one time, while she was pregnant -- one of our friends who has a kid was just saying, "You know it’s all about getting the baby on a schedule. That’s most important." And I remember Jessica saying, "Well, Eric and I just kinda go with the flow. We’re not really gonna enforce schedules." And now that she has Maxwell, I don’t think that we could be more on a schedule! Everything is scheduled. It’s fascinating to see Jessica organized and responsible.

So, she really has changed!
Now we’re not late for dinner reservations. We’re not late anywhere.

Has your friendship changed since she became a mom?
I’d like to say we’re closer. I’ve always looked at Jessica as a younger sister. When we met, she was 19 and I was 23, so I was going through way different things than what she was going through. Now the roles have totally changed. She talks to me about being a mom and being so happy and in love. It's just different 'cause I was always the more...I don’t even know how to explain without it sounding weird.

It's like she's have more grown-up experiences?
Yes. And she’s experiencing them first. Which is weird when I used to experience them first.

You mentioned that you love Eric as a partner for Jessica. How is he as a dad?
Oh he’s amazing. He’s great. He’s Superdad! I’ve never seen anything like it. He’s totally raised the bar amongst all of our friends. I tell my fiance [actor Donald Faison], I’m like, "You’re gonna be like that with our kid, right? 'Cause I’d be devastated if you weren't!"

You’re doing Weight Watchers with Jessica. How are you encouraging each other?
Well, she encourages me. I wish I could say I was encouraging her. She’s pretty much the inspiration and the leader in the whole group. If you would have asked me that when we started, I would have not been thinking that. But she works hard. She watches everything she does. She is really trying to be the best mom that she can be, and she’s in such a happy place that you can’t even compete with her.

You’re both engaged. Are you helping each other with wedding plans?
Well, I wish that we could say that we were planning stuff. I’ve been engaged a little over a year, and I don’t even have a date yet. It’s really been so much about Maxwell that we’re not even missing anything about planning a wedding. We just sit and play with the baby all the time. There's no rush.

How have you seen Jessica transform over the years?
I think the biggest change that I’ve seen -- especially now since the baby’s here and she’s been with Eric -- is that she has just found that confidence and happiness with herself. She’s just in the happiest place I’ve ever seen her in. Even on her worst day, she’s still happy with her life. If things get hard or rough, she’s just like, "Well, I’ve got Maxwell and I’ve got Eric. It’s never gonna be that bad."

Ali Gray is iVillage's Senior Associate Entertainment Editor. Follow her on Twitter: @thealigray

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