Looks like he’s not lucky in love – or blackjack. Just six days after Tony Romo broke up with Jessica Simpson, leaving her devastated, the Dallas Cowboys quarterback was spotted cruising the casinos in Lake Tahoe, Calif., on Wednesday.

In town for the American Century Championship golf tournament at the Edgewood Tahoe Golf Course, Romo, 29, enjoyed an early morning round of golf with two friends before trying his hand at poker, roulette and blackjack at Harrah’s and Harveys. Though he was losing most of his games, Romo joked with the dealers and was in good spirits as he nursed a cup of black coffee.

Later that same night, Romo emerged with a group of four friends at the Dennis Miller comedy show at Harrah’s. The group eventually made their way to the Cabo Wabo restaurant for a few rounds inside the VIP room before the NFL star called it quits just after 11 p.m.

Earlier in the week, Romo’s curfew was much later than that as he enjoyed a boys weekend in L.A., where his pals made their best efforts to “lift his spirits,” says a source. “His friends wanted him to have some fun before football training starts.”

They’ve got 13 days more days to do just that: Romo is due to report for pre-season training on July 29. Romo’s Cowboys coach Wade Phillips told People at the ESPY Awards Wednesday that he hasn’t spoken to the quarterback since his split from Simpson, “but we start camp in two weeks and he’ll be ready.”

Source, Fame Pictures

While Tony Romo is reveling in his renewed membership to the Singles-R-Us Club, Jessica Simpson is having a hard time coming to grips with being dumped a day before her 29th birthday.

“Jessica was really blindsided,” says a Simpson family friend. “She’s sad, mad, and confused. Her emotions are all over the place.”

Another source close to Simpson tells PEOPLE that “it’s been difficult lately” for the pair, who first started dating in November, 2007.

“Dating her comes along with her celebrity and press – that’s not easy for anyone,” says Simpson’s family friend. “But she and Tony seemingly had it figured out. They rolled with the punches and focused on each other. They just lost sight of that at the end.”

Since the sudden split, Simpson has been laying low. “She is holding up okay,” says the Simpson source. “She is with her family. They are – as always – very supportive of her.”

The one thing the family will not support: The thought of Simpson reconciling with her ex-husband Nick Lachey, who recently split from his girlfriend Vanessa Minnillo. “It won’t happen,” says a source. “They have no respect for him. Jessica has no respect for him. There is way too much bad blood between Nick and Joe for Jessica to even think about it.”

The Simpson clan, however, was upset to see Romo go. “Everyone really liked him,” says the Simpson family friend. Adds another source close to the Simpsons: “He wanted this perfect mold of the perfect football girlfriend. People don’t realize that Jessica has been worn down by Hollywood. She has insecurities and inner demons that she struggles with. She’s not some upbeat blond cheerleader that people want her to be.”

But Simpson is, if nothing else, strong. “She’s gone through heartache before,” says a source. “She wants someone who is on the same page that she is. If she has to move on for that, she will.”

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On what was supposed to be Jessica Simpson’s celebratory birthday weekend, Tony Romo was the one who seemed to be having the time of his life.

The Dallas Cowboys quarterback, 29, was spotted out at Hollywood hotspot MyHouse on Friday – the night he was supposed to be at Simpson’s 29th Barbie-and-Ken-themed birthday bash – for “a typical guys night out,” says one onlooker. “Tony’s table was packed with people. He was talking to several girls throughout the night.”

According to a source, his friends decided to take their recently single pal out to “lift his spirits. His friends wanted him to have some fun before football training camp starts.”

Done and done: Romo recovered from his late night Friday romp by lounging poolside with his pals at the Sunset Marquis Hotel in West Hollywood on Saturday afternoon. “The guys were mellow, had a few beers and Tony seemed fine,” says a witness. “There were no girls around. It seemed more like a relaxed boys weekend.”

By Monday the guys were recharged ready for more, hitting up West Hollywood’s Key Club – ironically the same place where Romo serenaded Simpson for her birthday last year. “The night was non-eventful,” says manager Mark “Skip” Bucculoa. “Tony stayed low-key. He just rolled in with a group of guys.”

Tuesday Romo was spotted rolling solo to L.A. shop Affliction, picking up some T-shirts and board-shorts. He reportedly shot a Pepsi commercial that morning and is expected in Tahoe for the Celebrity Golf Week July 14 through 19. No word on when the real Pepsi ad will air, but on FunnyOrDie.com a new Romo spoof popped up, highlighting the athlete’s comedic chops.

Regardless, Romo better take advantage of the free time while he can: The NFL star is set to start pre-season training on July 29.

Source, Bauer-Griffin

Two weeks ago, when People asked Tony Romo what he had planned for girlfriend Jessica Simpson’s birthday, he said, “It’s a secret.”

As it turned out, Simpson’s birthday surprise turned out to be a shocker: Although Romo had insisted that things between them were “going good,” the Dallas Cowboys quarterback ended their year-and-a-half relationship on July 9 – the night before the singer turned 29.

“She is heartbroken,” says a source. “She loves Tony. But it’s been difficult lately. He’s busy with his career and she’s getting ready to shoot her show (The Price of Beauty). They decided to part ways.”

But nobody would say that the pair didn’t give their relationship a good shot – weathering many a storm and breakup rumors before.

Early Romance
After Simpson and her family went to see Romo play for the first time in November 2007, things moved pretty quickly – he even kissed her on their first date!

“The fact that this guy, on our first date, in the first 10 minutes of dinner, wanted to lean over the table and say, ‘This is my girl and I want to kiss her’ – our first kiss in front of everybody – was awesome,” Simpson said at the time.

Days later, they shared Thanksgiving together in Texas – but their first bump in the road came quickly. In December, after Romo played his worst game ever while his new girlfriend looked on from the stands, some fans blamed Simpson for distracting Romo and causing the team to lose.

Still, the couple rebounded with a Mexican getaway, a romantic Valentine’s Day dinner and a public PDA session on his birthday (complete with a frosting fight) in April.

United Front
By May, rumors began to swirl that the couple was heading for a split and that Simpson was devastated to learn her ex-boyfriend, John Mayer, had started dating Jennifer Aniston. But her rep denied talk of a breakup, and Romo escorted Simpson to her sister Ashlee’s wedding that same month.

The summer seemed blissful for the couple: Simpson went home with her man to Wisconsin where they had dinner with his parents. Later, she dedicated her song, “You’re My Sunday,” to Romo during a concert tour for her country album and even gushed to People that he was “the love of my life.”

At the beginning of 2009, Romo stood by Simpson when she was slammed on blogs for looking heavier, even taking her out for a romantic night out in New York.

“I’ve never dated a guy that was more simple,” she swooned in the May issue of Vanity Fair. “I’m always there for him … And he knows he has me to come home to.”

Quick Split
In recent weeks, however, the couple have been spending time apart. A source tells People: “They’ve been having a lot of problems lately in general.” Their last public appearance together was July 1 when she sang the National Anthem at the National Golf Tournament in Bethesda, Md., and Romo played a practice round with Tiger Woods.

On July 2, Simpson still seemed upbeat and excited for her upcoming birthday. She posted a message on Twitter to her friend Emmy Rossum about her upcoming party: “Can’t wait to see your costume on the 10th! Birthday evite coming soon. You are always the best dressed!!!”

But just nine days later, Simpson ended up celebrating her birthday quietly “with family and close friends,” according to a source close to Simpson. Meanwhile, Romo was spotted out with a group of friends at L.A. hotspot MyHouse. According to a source, Romo was out with the guys to “lift his spirits.” Adds the source: “His friends wanted him to have some fun before football training camp starts.”

On Sunday, Simpson again took to Twitter to write this reflective post: “Everyone needs to know that hope floats … grab the strings and pull it back to you. Falling asleep with my mom and the dogs. Please lord give all of my beautiful fans, friends, enemies, and family rest. Bring all of us peace.”

Says the source close to Simpson: “[Jessica and Tony] were good together for along time. But I guess it wasn’t meant to be.”

Source, Bauer-Griffin

Tony Romo broke up with Jessica Simpson on Thursday, the night before her 29th birthday, a source close to the pop star tells PEOPLE.

“She is heartbroken,” says the source. “She loves Tony. But it’s been difficult lately. He’s busy with his career and she’s getting ready to shoot her show (The Price of Beauty). They decided to part ways.”

The Dallas Cowboys quarterback fueled breakup rumors when he showed up with about 14 friends at the Hollywood hotspot MyHouse on Friday night without the birthday girl, a source tells PEOPLE.

“He had quite a few girls stop by his dance floor table,” says an onlooker. “Romo was sipping Grey Goose and having a fun time with the boys.”

Simpson’s rep had no comment. Romo’s rep could not be reached for comment.

Simpson had planned to throw a Barbie and Ken-themed party for her birthday, but it fell through, according to a message she wrote on her Twitter page Saturday. “Barbie party didn’t happen, but I turned 29 and feel like I am on top of the world yelling I LOVE GETTING OLDER!” she wrote.

On Saturday night, Romo spoke to a group of well-heeled sports memorabilia collectors at the Los Angeles Sports Museum of Los Angeles. He “blushed” when a woman asked about his relationship with Jessica Simpson, according to the L.A. Daily News.

The source close to Simpson is sad that the longtime couple broke up. “They were good together for along time,” says the source. “But I guess it wasn’t meant to be.”

Although Simpson’s heart might be broken, she seems to remain hopeful about love. On Sunday, she Tweeted, “Everyone needs to know that hope floats … grab the strings and pull it back to you.” Three hours later, she wrote, “Falling asleep with my mom and the dogs. Please lord give all of my beautiful fans, friends, enemies, and family rest. Bring all of us peace.”

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Do you like her dress?

Following a year of dodgy performances, Jessica Simpson picked up the mic again to perform the National Anthem Wednesday at the opening ceremony of the Tiger Tourney. She wore a hip-hugging red-and-blue striped dress.

The singer – whose beau Tony Romo participated in the Tiger Woods event – “eventually left the first green before any of her body parts managed to escape,” notes the Washington Post.

Simpson was greeted by a slew of photographers when she first arrived in Washington D.C. Tuesday.

She was jokingly asked if she’s waiting for Romo to win a Super Bowl before she agrees to marry him.

Simpson (who turns 29 July 10) replied, “He’ll win. Tony is playing with Tiger tomorrow. That’s all I’m thinking about.”

Romo recently addressed marriage rumors.

There are “none that I can think of,” he told Entertainment Tonight. “I’m sure you guys can tell me something new here soon enough, though.”

Last week, Simpson confirmed Us Weekly’s original report that she is doing another reality show. The Price of Beauty, which will follow the singer as she travels around the world in search of what people find beautiful, debuts on VH1 in 2010.

Source, Bauer-Griffin