
Babe Bennett wasn’t my favorite love interest for Adam Sandler but I do really like Winona Ryder. This is also right before she nearly ended her career with some bizarre shoplifting arrest. Only bouncing back after she secured the role of the mom on the Netflix hit Stranger Things

She’s a beautiful but not super well known reporter for some trashy news site that probably has slightly more integrity than Fox News.

And she pretends to be romantically interested in Deeds for an undercover story.

But ends up actually falling in love with him and regretting everything.

She even nearly drowns in a frozen pond because Deeds thought it was all an act.

But using her actual real journalism talent, she was able to figure out that Arthur Blake had a secret son which saved Blake media from being destroyed by Chuck Cedar and (presumably) has a happy ending with Deeds.