Were 80s/90s magazine contests legit and did anyone actually win them?

Two examples: https://imgur.com/a/7iQRNWi

The first example is hilarious, David Lascher calling young women around America to ask a question (I'm guessing pre-recorded) and the winner is flown out to a dinner in Hollywood. Did that actually happen?

Second example is tech and computer stuff, except it asks for money to enter, which I've never seen before. That's a bit of a red flag.

I remember contests all the time in magazines I used to read... but you never hear about them ever again.