5 Dating Lessons from “To Rome With Love”

Posted by in love after 40, single women over 40 | 0 comments

Rome ~ an enchanting city with its ancient ruins, beautiful gardens, and the possibility of romance around every corner. At least that’s the way Rome is portrayed in this summer’s blockbuster movie, To Rome With Love. Once again, Woody Allen has woven together a comedic tale of misunderstandings, unmet dreams, love  and possibilities. Most of all, this is a story of love and how perspective can change everything.

Alec Baldwin plays a famous architect, John, who lived in Rome as a young man. He meets Jack (Jesse Eisenberg), a burgeoning young architect who’s studying in Rome and lives on the same street that John did in his youth. Jack’s girlfriend Sally’s (Greta Gerwig) good friend comes to stay with them, and soon Jack finds himself in love with the flirtatious and duplicitous Monica (Ellen Page).

John had experienced a similar relationship way back when, and tries to warn Jack of the impending doom. He acts as a voice from the future, lurking invisibly in the background, trying to warm Jack of the huge mistake he is making in falling for Monica.

While the movie weaves together a chain of other comical relationships with twists and turns that keep it surprising, I want to focus on the relationship between Jack and Monica.

Let’s take our main character, Jack, a seemingly rational ‘good guy’ with a lovely girlfriend. They live together in Rome in a seemingly idyllic lifestyle. They are bohemian artists, living the romantic life in a foreign culture. What could be better?

Monica comes to town, and Sally has her reservations about the whole thing. She knows Monica’s history; men fall in love with her. She has that certain je ne sais quoi about her. She is not the most beautiful woman. She is not the brightest or the most witty. But she knows how to work it! She’s a player.

I was fascinated with the allure of her character as I watched the movie yesterday. Monica is just self-deprecating enough to be charming. She listens to Jack with rapt attention, and validates and acknowledges him a lot. She is fun, always up for an adventure. And she fakes it well; she knows one line from many romantic poems and works of literature. She knows a few architect’s names and drops them like she’s well-acquainted with them.

John, older and wiser, stands by and smells the lies and manipulation. He tries to warm Jack, but to no avail. Jack is a goner, hooked on Monica and he can’t hear the voice of reason.

What happens next are a series of crazy events that almost ruin Jack’s life.

I won’t tell you the ending. Go see it for yourself. But I will share what I learned from the movie.

Dating lessons learned from To Rome With Love

1. Go into every relationship with eyes wide open.

2. Pay attention to your intuition (or your good friends) when the warning bells go off.

3. If it’s too good to be true, it probably is.

4. Value the good people in your life, not the most exciting ones.

5. Don’t lie or cheat. You’re only hurting yourself and those you love.

So, please go see To Rome With Love, and let me know what dating lessons you learned from the movie.




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