I want to know what ideas he discarded before deciding this was the best one.

Kind of goes along the lines of why guys honk at women and actually expect a positive reaction, that is the best idea they have,

My neighbor married a girl and he was two years older than her parents. She's now a good looking widow with money in the bank. She really loved him though, she basically had a mental breakdown when he died from grief.

Winning!

Oh, for sure, and nobody has ever accused me of being a hopeless romantic - I'm far more likely to see an opportunity to snark than see romance in the various shit people do in the name of love.

Out of curiosity, now old was this dude? I'm not sure what a 'good' (less bad) age would be, but if he's in his 30s or something, jesus fuck it's pathetic and creepy, and if he's in high school maybe just pathetic (as well as way premature). It seems like there would be a very narrow window of time when this would have any chance of coming off as somewhat normal/romantic.