Now there are lists a-plenty, and everyone has their preferences, but I’m sure that no-one would disagree with the five films I’ve listed below. I will state up front though that these are from a guy’s perspective as I’m sure some ladies might have different selections.
An oldie but a goodie! (Poor) Boy meets (Rich) Girl on a romantic cruise. What could be more perfect? Well, there is also the giant iceberg and the fact that almost 70% of the people died!
Leonardo DiCaprio (Jack) and Kate Winslet (Rose) are our two main protagonists in this film, and they both do a stellar job. While you’d hope for a happy ending and of course questions still abound about the size of the wooden panel that Rose is clinging on to and why Jack couldn’t save himself also. I think in terms of romanticizing this tragedy while at the same time educating a generation, Titanic ticked all of the boxes!
You can stream Titanic on Amazon.
This time it’s a bit of a twist. Rich Boy meets Poor Girl. Of course, the poor girl, in this case, is Vivian played by Julia Roberts and she could be referred to as a “lady of the night” or perhaps more colloquially as a hooker! Richard Gere playing Edward is an extremely wealthy businessman. While a nice guy personally, his focus is very much on taking companies and breaking them up into their constituent parts – regardless of the impact that has on the common man.
The updated Cinderella Story has Vivian changing Edward and making him realize that there is more to life than money. This was my first introduction to Julia Robert’s dazzling smile which we’ve all come to love and enjoy, and it was an entertaining film!
You can stream Pretty Woman on Amazon.
Bridget Jones’s Diary
The most recent movie on our list with a release date of 2001, Bridget Jone’s Diary is also probably the funniest. Renee Zellweger is simply fantastic as Bridget as she documents the trials and tribulations in her life as she searches for love in London.
With Colin Firth and Hugh Grant as her prospective suitors, Bridget Jones’s Diary is based on the book of the same name by Helen Fielding. A reinterpretation of the classic Pride and Prejudice, this movie will have you giggling and guffawing while at the same rooting our heroine on!
Sleepless in Seattle
At the time it seemed almost every other movie had either Tom Hanks or Meg Ryan. However, this was the first where they were thrown together. Tom plays the part of widower Sam Baldwin and when his son Jonah calls into a talk-radio show to find a new wife for his dad, the women all over America swoon.
One of the listeners is Annie Reed played by Meg Ryan. A reporter based in Baltimore, she falls for Sam and asks to meet him – at the Empire State Building on Valentine’s Day.
You can stream Sleepless In Seattle on Amazon.
The Princess Bride
While my mentioning the Empire State Building might have led you to think my next choice would be the classic Cary Grant film – An Affair to Remember – I’m going to take you in a slightly different direction.
The Princess Bride is the oldest film on my list with a release date of 1987, but that just means its one that I’ve watched the most! This film appeals to all and has everything you could ask for. With true love, sword fighting, monster bashing and a literal return from death – you really couldn’t ask for more in a romantic movie.
Celebrating its 30th anniversary in September of last year the Princess Bride rightly deserves its place at the top of my list!
You can stream The Princess Bride on Amazon.
Special Mention: The Big Sick
This is the most recent movie on the list. 2017’s The Big Sick is a modern romantic comedy based on the relationship of the writers of the film, Kumail Nanjiani and Emily Gordon. Shortly after meeting and falling in love Kumail and Emily, played by Zoe Kazan, break up. After the break-up Emily suffers a life-threatening illness and put into a medically induced coma. During the coma Kumail cares for Emily and grows close with her Parents played by Ray Romano and Holly Hunter.
The Big Sick also deals with cultural issues. Kumail and his family are originally from Pakistan and his family wants him to marry a Pakistani woman. His relationship causes a rift between him those closest to him.
It’s definitely worth a watch.
You can stream The Big Sick on Amazon.