Canonically: Hugh proposed to Lila at a hotel inn. (I thought that was so cute!!)
My headcanon for a future comic: Hugh worked as a custodian at the hotel Lila was staying at during her business trip. (Maybe as an intern since I'm picturing early/mid-twenties. haven't decided)
It was a love at first sight situation for Hugh. (I picture him having a thing for the business busy-body types)
Hugh being a sweetheart and awkward little charmer while Lila is working in the lobby/lounge by herself.
During her stay, he notices she doesn't really stop working, eats microwavable meals and snacks on the go often. So, he decides to bring her a bento with his signature meatloaf in it, in which she instantly falls in love with!