22. Vince Vaughn and Kyla Weber

Since celebrities have such a large pool of possible romantic partners, it’s always intriguing when they start dating someone who isn’t popular. When Vince Vaughn became associated with Kyla Weber, it seemed remarkable that a non-famous individual was able to catch his eye. If you think Weber is an unremarkable individual, you’re in for a big surprise. Weber seems to be doing well in the real estate industry, and she was reportedly able to sell a lot of investment properties in California, where she now lives with her husband.

Vince and Kyla met after one of his friends introduced him to her. Vaughn and Weber’s relationship heated up after that first encounter, and she officially flew to Chicago to meet his parents four months into their relationship. The pair married the following year after getting engaged in 2009, and according to sources, they celebrated their wedding for three days. They have two children, Locklyn Kyla and Vernon Lindsay.