Jennifer Love Hewitt And Will Friedle

Jennifer Love Hewitt has had success with several different roles throughout her career that made her one of the biggest stars of the ’90s and early ‘2000’s. Perhaps that’s what helped draw her towards Will Friedle, who you may instantly have recognized from his role on Boy Meets World.

The two were allegedly dating for a short time back in 1997. Judging from their attire, it definitely looks like they elected to date during the Fall/Winter seasons!

But even if their sweaters were managing to keep them looking warm, they’re still not the most stylish. She even appeared on one of the episodes of the show, for the Halloween themed one.

Naturally, when she was on it, it was love at first sight for the characters and they immediately took to each other.