When he meets his holiday romance at the same hotel from 20 years ago, a broke Greek waiter must help organize her wedding to one of the most wealthy and prominent men in the country. (For the YouTube livestream)

How about:

Twenty years after she rejects his marriage proposal, a poor waiter tries again while organizing her wedding to a well-heeled suitor.
(21 words)

Is it in the ballpark of the story you want to tell?

>>> while secretly trying to break them up.?

My concern is that it focuses on the negative side of what must surely be his positive intent.? ?Yes, he has to break them up but that’s only 1/2 the job.? He could break them up? and still fail to win her heart.

His ultimate objective goal is to win her heart.? So I suggest the logline should be framed positively, in terms of his end game, his ultimate goal.

Further, I don’t think the rival? needs to be described in? negative terms like “conceited”.? It facilely sets him up as? a dramatic foil.

He could be a perfectly decent guy — but it’s just not a match.? ?There’s no personal chemistry between them. (As there still is after all these years between her and the waiter.)? It may be a marriage of material convenience for her.? She’s the one with the character flaw:? she’s settling for security instead of? daring to risk all for love? (which is why she turned down the poor waiter the first time).

I suggest this is a more mature story line, an emotionally seasoned one that would appeal to the obvious target audience. (By obvious, I mean the passage of time, 20 years, places the characters in the 40+ age group.)? ?An audience that has lived and loved long enough to have faced such a predicament or know of friends or family who have.? They can connect and empathize with the dilemma faced by both of the principal characters.

fwiw