The May-December Marriage Ender: Latest Threat to Hollywood Relationships

Camille Donatacci and Kelsey Grammer. Click here to see photos of Kayte Walsh.

But in June, their seemingly sublime partnership fell apart. Donatacci filed for divorce, citing irreconcileable differences, claiming Grammer didn't talk to his children on Father's Day, and requesting primary custody of them along with spousal support. While Grammer took to his blog to accuse Donatacci of spreading "malicious and unfounded rumors" about his parenting abilities, a side story bubbled up: that he was dating a British flight attendant, Kayte Walsh, 29. Paparazzi snapped the two getting cozy in New York. And last week, the Daily Mail reported that they're expecting a child.

Maybe it's a male comedian thing -- Grammer, Armisen, and of course, the Godfather of the May-December marriage ender, Woody Allen -- all have a knack for making people laugh and wooing the young'uns.

3. Before: Susan Sarandon and Tim Robbins. After: Susan Sarandon and Jonathan Bricklin?

Then again, women can play this game too. Though they never married, Sarandon, 63, and Robbins, 51, were noted for maintaining their relationship in an industry where hooking up and breaking up can seem as routine as a trip to the gym. Beyond excelling at acting, they bonded over political causes, taking a stance against many of the policies of former President George W. Bush. In their heyday, Sarandon and Robbins frequented fancy red carpet affairs as frequently as they did low-key charity events and fundraisers.

With connections on so many levels, marriage was never a priority for the couple.

"I won't marry because I am too afraid of taking him for granted or him taking me for granted," Sarandon said once, according to People magazine. "Maybe it will be a good excuse for a party when I am 80."

The party got canceled in December 2009, when Sarandon's rep announced that the couple had ended their 23-year-long relationship over the summer. Since then, she and her business partner, 31-year-old Jonathan Bricklin, have been joined at the hip. The two are co-investors in SPiN, a New York City ping-pong club, and are working on a reality TV show based on it. Now, it appears business has become pleasure: this summer, photogs snapped Sarandon and Bricklin traveling through Italy and Peru.

Susan Sarandon, Tim Robbins, and Jonathan Bricklin.

Both maintain they're not dating. But romantic or not, Bricklin certainly seems to have filled a role in in the Oscar-winning actress' life previously played by Robbins. In March, he had some pretty kind things to say about Sarandon. Professional praise or not-so-lucid love letter? You be the judge:

"She's amazing and I'm so lucky to be her business partner," Bricklin told The New York Observer. "We have a great relationship. I've gone on trips with her to meet with ping-pong players, and she has been extremely generous with her time. She's one of my closest friends now. But as far as a romantic relationship, we are not having one. I'm flattered people think that we might be."

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