drain

Good evening everyone, Was doing the first oil change after 50hrs on my 1969 Arrow 200 (IO360 C1C). I unscrewed the gold cap of the drain plug and pushed up on the inner cylinder to let the oil drain. All was fine and the oil came out, however once I went to let the plug down it just won't come...

My daughter has a 2014 Ford Fiesta. Got it 1 year ago and it had a new battery put on at that time. In the last month, it has been dead three times when she goes to start it. She generally drives every day, but each of these times the car did sit for 2-3 days. I'm having a shop look at it now...