Why Date Him?
Sorry to be a nay-sayer, but he's a friggin' stalker. Guys with stalking tendencies?! Ugh. Wouldn't you find it weird in our not-so-ideal-not-so-romantic life?
And on top of that, you could tell if someone falls in love with you without knowing who you are and continues to push so hard, they are not respecting your personal boundary, let alone to know how to love you properly. The woman has baggages and needs baby steps. However, he agitates me by doing the exact opposite: within such a short period of time, he wants her to meet the parents even though she is entirely uncomfortable with the idea and changed her mind a few times. He becomes even more inconsiderate and insensitive when he puts her on the spot by proposing to her in front of his family. Any regular woman would have been scared off right away, run far from his needy "I can't lose you", and it's a miracle Lisa still sticks around.
Like some people noticed, the duo have little chemistry, and I can only feel it when Mary Stu's character becomes shy, nervous, embarrassed and frustrated. Before the couple have the X-mas argument scene outside his house, I donn't see much sparkling from her part or his. It is entirely odd and incomprehensible that her character just reaches a conclusion and suddenly blurts out she loves him after a long wander.
My conclusion:
Guy needs a therapist and a date coach on how not to stifle the woman he dates and how to deal with his own widower status and marriage fetish.
Girl needs a therapist to deal with her upbringing and insecurities, and every other issue she has, such as why she couldn't break off with her ex-boyfriend even both did not desire to be each other.
The couple also need some couple therapy. But before they start dating, they should get their own problems out of the way so they know how to love.
The movie is a mess, and I don't see anything romantic. They should just end right when their fantasy bubble bursts.
I don't intend to be offensive, but I have to defend my opinions.