Barbra Streisand and James Brolin – 23 Years
Did someone say power couple? Yep, Barbra Streisand and James Brolin are nothing short of legendary names in the entertainment industry. The two A-listers were actually set up at a party, and they clicked immediately! Soon after in 1996, they went on their first date. Two years later, the happy couple got married.

Looking back on their first date, Barbra has fond memories. As she explained in an interview, “I met him at a dinner and expected a bearded mountain-man type, and he had cut off all his hair and was clean-shaven.” Clearly, James’s unexpected appearance didn’t cause any issues for the pair, considering they’ve been together for over 20 years now!