I caught this on a flight the other day and wow... just wow. It's AWFUL but in a cringey amusing way.
The most glaring thing about it was definitely all the ridiculous gender roles and stereotypes here, especially when it comes to the female characters who are portrayed to be either batshit insane, desperate or both. It was only made 11 years ago, but we're truly living in a different era. I was shocked to learn a woman co-wrote the script.
Other fun things:
lack of any central character (there's about 10 that we have to keep track of),
prevalence & importance of flip phones, and how much emphasis is put on phone calls in general
the internet is referenced in a way that shows the writers clearly dont understand it
"man on the street" style 'interviews' with strangers yapping about their thoughts on dating thrown in randomly throughout the movie