Jay Cutler

Kristin Cavallari arriving on a flight at LAX airport (2/4)

Remember when Kristin Cavallari got engaged to Jay Cutler back in 2011, dumped a few months later, and then reengaged a few months after that. Kristin tells E! the second engagement was even more romantic than you can imagine:

"It was so silly. I was in the airport, leaving Chicago. We had just spent however many days together and we were texting and somehow it came up, like, 'Oh, shall we get married?' We're like, 'Yeah, OK.' And then he sent my ring in the mail. So I actually had my ring sitting at home for a couple of weeks before I put it on."

Mailing an engagement ring to your fiancee may seem pretty lame, but in Jay's defense, Kristin is a reality star, which ranks slightly ahead of "child molester" on the list of the lowest of all human lifeforms. They're so undeserving of love that it's actually still legal to shoot them in three states. God bless you Montana and the Dakotas.

*15 Kristin Cavallari pictures total in the gallery:

Jay Cutler and Kristin Cavallari out and about in Chicago (5/2)

Jay Cutler decided to go all tough guy on the paparazzi last week during a walk in Chicago with his pregnant fiance Kristin Cavallari. And I don't think it worked. I've been more intimidated by Girl Scouts selling Thin Mints.

*20 Jay Cutler pictures total in the gallery:

Kristin Cavallari out and about in West Hollywood (4/11)

I wish there was a way I could bet on Kristin Cavallari getting dumped right after she gives birth to Jay Cutler's baby, because I would literally make a kajillion dollars. From the New York Post:

Kristin Cavallari is five months pregnant with the child of Chicago Bears quarterback Jay Cutler, but she's waiting to get married until after their baby is born. At the Conde Nast Traveler Hot List party in Los Angeles, Cavallari was overheard telling Jessica Alba that the couple is "focusing on the baby. Neither one of us have any religious reasons for why we need to be married right [now], and I don't really want to be a pregnant bride. We will focus on that after the baby."

Ah, I can see the big day already. There's the beautiful bride Kristin Cavallari, being walked down the aisle by dear ol' dad to a beaming Jay Cutler, ready to make the plunge. "With this ring, I take Kristin..." FUMBLE! FUMBLE! Jay fumbles the ring and amidst the pandemonium of NFL busts and reality TV stars, slips out the back door, and runs to the Canadian Football League, leaving pregnant-as-fuck Kristin at the altar looking all sorts of stupid. Well, what did you expect from a colossal choke artist like Jay? I'm sorry for the cheap shots but this teabagger cost me $5k in '10 when he shit the bed against Green Bay. F'n idiot, my car got repossessed because of you, you prick. In only nine more payments, that '87 Chevette would have been all mine, baby.

*32 Kristin Cavallari pictures total in the gallery:

Kristin Cavallari leaving Erewhon Natural Food Market in West Hollywood (1/21)

Just a few months after getting reengaged to Chicago Bears' quarterback Jay Cutler (he dumped her in June, possibly in the middle of her trying on wedding dresses), Kristin Cavallari is pregnant. "Let's see that asshole dump me this time!" The couple told People:

"We are thrilled to announce we are expecting our first child together. It's an amazing time in our life and we can't wait to meet the new addition to our growing family."

[insert joke about Jay Cutler finally hitting a target and not cumming way over Kristin's head here]

*11 Kristin Cavallari pictures total in the gallery:

Kristin Cavallari shopping in Beverly Hills (11/7)

Is Kristin Cavallari cursed? Yes, yes she is. What, you think it's mere coincidence that as soon as Jay Cutler gets reengaged to her, he breaks his thumb and is out for the season? Just watch. As soon as these two are officially married, I bet Jay gets a nasty infection in his vagina. From Life & Style:

Kristin Cavallari and Jay Cutler are engaged—again! After calling off his three-month engagement to Kristin on July 23, Life & Style can exclusively reveal that Jay has proposed for the second time—and Kristin has accepted!

"Kristin is over the moon with happiness," a source tells Life & Style. "She's already told her friends that the engagement is back on. They haven't set a new date yet."

It's sweet how things all work out in the end sometimes. Now that Jay's broken his thumb and Kristen is no longer able to find work, the two of them should have plenty of time to plan their "dream" wedding. Even more fortuitous for Kristen is the fact that she'll be able to ask Jay for advice on how to throw the bouquet. They'll just have to make sure that all of the single ladies are wearing the opposing team's jersey.

Seriously, I fucking hate him.

*12 Kristin Cavallari pictures total in the gallery:

Kristin Cavallari and Jay Cutler back together

After being dumped in an especially cruel way by him a few months ago, Kristin Cavallari somehow found it in her heart to forgive Jay Cutler and the two are now back together. Also, she had rent due so what the hell was she supposed to do? From the Chicago Sun Times:

It sure seems like the Jay Cutler-Kristin Cavallari reconciliation is continuing right on track, with the actress back in town and seen with her ex-fiance all over town, including a cozy sighting at Public House over the weekend. Friends of the reconnected couple say the duo are taking it slowly but are happy to be back together.

What a shock -- now that the football season is in full swing and no longer in peril of a work stoppage, Kristen is once again dating Jay. I wonder what the motivation could be behind this reconciliation? Hint: $$$$. I guess this just shows that when an attention-seeking reality star dates a professional athlete, she only wants to be with the ones that are actually working -- which means Kris Humphries better start looking for a good divorce lawyer.

*31 Kristin Cavallari pictures total in the gallery:

Awk. Ward.

Kristin Cavallari may not be having a wedding but she'll always have the wedding dress pictures. Awk. Ward. From Life & Style:

Just two days before Kristin Cavallari’s fiancé, Jay Cutler, broke off their engagement, she was glowing with excitement while trying on a series of wedding dresses at her exclusive Life & Style photo shoot. The reality star looked dazzling in gowns by Anne Bowen and Mon Cheri Bridals as she gushed about her plans for a traditional wedding and her vision of walking down the aisle in a strapless gown. “I want a romantic, mystical wedding, with lots of flowers,” she shared with Life & Style during the shoot at LA’s Mondrian Hotel on July 21

Now, an insider close to Kristin reveals that the real trouble began the very next day—on July 22—when Jay asked her to fly back to Chicago with him the following morning.

“Kristin said she didn’t want to because she’s working on a new TV project and had a full day of shooting scheduled for Tuesday [July 26],” the insider explains. But Jay was angry about it and the argument escalated. “He told her that she needed to commit to him, and to move to Chicago,” the insider continues.  When it became clear that Kristin had no intention of giving up her career in entertainment, Jay broke up with her — returning to Chicago alone on July 23.

Shouldn't you know whether or not your soon-to-be spouse will be willing to give up their career BEFORE you ask them to marry you? That seems like a pretty important initial conversation to have. If Jay just wanted a trophy wife that was blonde and completely worthless, he should have ignored Kristen in the first place and just proposed to Camille Grammer.

*5 Kristin Cavallari pictures total in the gallery:

Jay Cutler calls off wedding to Kristin Cavallari

"So about that whole wedding thing . . . yeeeeeeeeeeah . . . we're gonna go ahead and not do that anymore." From People:

This is not the fairy-tale ending Kristin Cavallari was hoping for. After just 10 months together, Cavallari and Chicago Bears quarterback Jay Cutler have called off their engagement, a source confirms.

"She got dumped," says a source. "She's absolutely devastated. She can't believe this is happening. She was planning her dream wedding, the date was set, the location - everything was set. She's in shock that the dream wedding she was planning is going to end this way."

Kristin is "absolutely devastated" and "can't believe this is happening." Coincidentally, most Chicago Bears' fans had that same reaction after they traded for Jay Cutler in 2009. "You mean that smug douchebag who likes throwing into triple coverage is on our team now? Aw god dammit."

*39 Kristin Cavallari pictures total in the gallery:

Jay Cutler and Kristin Cavallari at the premiere of Source Code in L.A. (3/28)

I'm sure you already heard about this because of the Google Alert you have set for "Kristin Cavallari and Jay Cutler" but the two are getting married. The Chicago Bears quarterback popped the question to the former star of The Hills over the weekend in Cabo San Lucas, Mexico. 100% true story: My friend made out with Kristin last year at a party at Coachella and she could not stop talking about how much money she made, how much money she was going to make, how much she made in the past, yada yada yada you get the picture. I guess the point I'm trying to make here is that Jay doesn't just make bad decisions in the pocket.

*25 Jay Cutler and Kristin Cavallari pictures total in the gallery:

Kristin Cavallari at The Bank Nightclub at the Bellagio in Las Vegas (1/15)

Kristin Cavallari has some exciting [and profitable] news! She's in love with Jay Cutler ['s paycheck]. From People:

"I'm in love," she told People Saturday night at Las Vegas's The Bank Nightclub while celebrating her 24th birthday.

Sadly, the object of her affection wasn't by her side. [Jay Cutler] has an excuse though - his team is in the NFL playoffs and played (and won) Sunday against the Seattle Seahawks.

"I want to be there," she said. "I'm bummed that I'm not there and he's not here. Things are really good. I'm just enjoying my personal life and taking a little time away from the public eye, which is why Chicago is great for me. My mom and that whole side of the family is there. And Jay is there. It's nice to be able to hang out with my mom, and, you know, I'm in love and it's been great."

Awwww, how sweet. Surely the messy break-ups of other reality stars with their NFL boyfriends -- like Kim Kardashian and Jessica Simpson -- won't happen to Kristin. Jay's unwavering commitment to her will undoubtedly prevail and last for an eternity . . . which in the NFL means until he has a road game and meets a slutty groupie in the hotel bar. "Blowjob time!"

*23 Kristin Cavallari pictures total in the gallery: