Jimmy Couldn’t Catch Margaret Sullivan
Jimmy Stewart didn’t walk down the aisle until he was a bit older. It could have happened sooner, but life had different plans. Sad, I know. But not all men back in those days were looking for a wife, especially not men like Jimmy Stewart. That was until he met Margaret Sullivan.

Stewart had a big crush on actress Margaret Sullavan. They met in college, and he was smitten right away. He tried his best to win her over, but she just didn’t feel the same way. Ouch. They stayed close friends, though, which is remarkable considering she married Stewart’s agent in 1936. Maybe that heartbreak is why Stewart stayed single for so long.