Sylvester Stallone & Jennifer Flavin – 22 years

Sylvester Stallone is known internationally for his lead roles in the blockbuster movies Rambo and Rocky. Jennifer Flavin, on the other hand, is an entrepreneur. They first met and started dating in the ‘80s. There was a time that they needed to take a break in their relationship when it was rumored that Sylvester had an affair in 1994. The year after, the couple got back together and got married in 1997.

It would be easier to say that the couple has the happiest marriage, but their love story is far from perfect. They went through a very rocky road, but it only makes their relationship last longer. They have been together for more than two decades, and it will surely last for a lifetime. They now have three daughters together. Jennifer continues to grow her investments as an entrepreneur, while Sylvester has been teasing fans about him reprising his most iconic role in the new and upcoming Rambo movie.