Despite the fact that a wedding is more about fun and entertainment (and marriage is merely a legal formality), it is still the most important event in a couple's life (and cause for wedding stress as reported by Rebecca Romjin). What that means is that you have to really plan it out so that it can be a moment of joy for the couple and their friends and family.

Is that what Usher was hoping to do?

That is what it looks like but it also seems that he was dating a much older woman Tameka Foster and she also became pregnant with his child (though Usher is clearly responsible for this). None of this made his family happy (especially his mother Jonetta Patton was very unhappy), though, you wonder if they have any business having an opinion on this.

What is horrible is that the wedding was canceled. While a cancellation like this can be devastating for the couple, it is much better than getting a divorce later.