The ultimate list of must-see romantic movies

Audrey Claire, My Wingwoman Founder & Coach
Feb 19, 2019

I have a GNI (girl’s night in) on the weekend and I’m in the mood for a good romantic flick. My favourite genre of film is actually action/adventure but who doesn’t love a good rom-com or dra-mance (drama/romance) on occasion?

Here’s a list of some of must-see romantic movies:

About Time (2013)

This has to be one of the most terribly under-rated romantic comedies ever. About Time is directed by Richard Curtis (who also made Love Actually and Four Weddings & a Funeral) and follows the life of Tim, a man blessed/ cursed with a special power that allows him to time-travel. No summary will do this film justice. It’s a poetic, funny and sincere film about love, time, aging, loss and everything in between. I loved every minute.

Pretty Woman (1990)

This movie managed to make prostitution seem glamorous and that’s quite a tall order! Richard Gere plays Edward, a wealthy businessman who is in L.A. on business for the week. Edward meets Vivian (Julia Roberts), a prostitute who comes to the rescue when Edward finds himself lost in his fancy car on the mean streets of Los Angeles. Vivan gives him directions, then a blow job, and by some miracle this movie ends up being incredibly romantic, memorable and one of the all-time classic romantic movies of all time.

Under the Tuscan Sun (2003)

I’ll sum this movie up in a few words: new beginnings, Italy, Italian men, flings, romance, Italian food and did I say Italy? This is an uncomplicated movie full of just plain good feels.

I Feel Pretty (2018)

Amy Schumer plays an insecure, slightly superficial woman who suddenly finds herself under a magic spell that makes her think that she has the looks of a super model. I loved the message about inner confidence this movie projects and Amy Schumer makes literally every moment funny.

Unfaithful (2002)

There is something deeply moving and sophisticated about this film which isn’t surprising as it’s directed by one of the masters of the genre, Adrian Lynne (of Fatal Attraction and Indecent Proposal fame). There is a darker romantic drama/ thriller vibe to this film. It stars Diane Lane and Richard Gere who play a happy and successful couple living on the outskirts of New York City. Things start to take an unexpected turn when Diane’s character starts cheating on her husband with a sexy and mysterious Frenchman. If you can’t stand hot and steamy sex scenes, this film isn’t for you (lol).

Forrest Gump (1994)

This movie has something for everyone: action, humour, romance, drama, history. The central story is about intellectually challenged Forrest Gump (Tom Hanks) and Jenny ‘Jernaay’ (Robin Wright) and how their lives diverge and converge over years and years. There are some incredibly romantic and sweet moments in this movie and it’s worth watching just for the tear-jerking cuteness in the last few scenes alone. One of my favourite heart-melting parts in the movie is a moment where Forrest says to Jenny: “I may not be a smart man, but I know what love is.”

Love Actually (2003)

Okay if you haven’t seen this movie stop reading this blog and watch it right now. This movie has something for everyone in it and I would describe it as witty, clever, moving, nostalgic, heart-warming and Christmassy. Also, this movie was written by one of the masters of Rom-Com (Richard Curtis) who, seriously, knows how to make you laugh one minute and cry the next. I love that this movie has an ensemble cast of so many great actors including Hugh Grant, Liam Neeson, Colin Firth, Kiera Knightley and Emma Thompson.

Notting Hill (1999)

This is a classic boy-meets-girl romantic comedy following Hugh Grant’s character, William as he pursues Julia Robert’s character, Anna. This film schools every man about the fact a woman can indeed fall for any man if he’s got solid character. You see William pursues Anna even though she is a mega film star (a bit like Julia Roberts herself) and William is just a regular guy next door.

Dirty Dancing (1987)

If you’re over 30 and you’re yet to see this movie, do yourself a favour and watch it ASAP. This movie ticks two major boxes: epic dance sequences and Patrick Swayze.

Breakfast at Tiffany’s (1961)

This is one of Audrey Hepburn’s most famous movies and it is a genuine classic. When you attempt to summarise the plot, it does seem a bit random (you’ll have to watch it to know what I mean), but in essence it’s about Audrey Hepburn’s character, Holly, who is ambitious, money-hungry and naïve. She lives in New York with her crazy cat (without a name) and a fabulous turquoise sleeping mask. One day she meets Paul and she has to choose between men of wealth and a man of character.

Out of Africa (1985)

This is one of those romantic movies I think you’ll enjoy more on your own, one lazy rainy Sunday arvo or on your next sick day. This film would have been epic at the time and it stars two legendary actors: Robert Redford and Meryl Streep. If you like epic period movies, definitely give this one a look.

The American President (1995)

In this movie Michael Douglas plays a widowed American President who falls in love while in office. There’s something cute and novel about this movie as you get to imagine a) that the President isn’t a blithering orange idiot and b) what it would be like to date him! You might find this film a little soothing as you allow yourself to pretend for a couple hours how much better it would be if literally anyone else were President.

Titanic (1997)

I still can’t believe this movie is 22 years old! It does make sense when I recall watching this movie as a teenage girl surrounded by my besties who had also seen this movie 100 times already by the time it came out on video (yes video, not DVD).

This is undoubtedly the movie that rocketed Leo Dicaprio to posters on our bedroom walls as well as the stardom he enjoys today. Kate Winslet is mature beyond her years in this film. Next time you watch it, remember she was only 20 years old filming this epic movie.

The Bridges of Madison County (1995)

This is a CLASSIC romantic movie. It honestly does not get much more romantic than this. If you’ve come across this before and dismissed it because it looked boring or outdated, please do give it a second chance. You won’t be disappointed. This movie stars Clint Eastwood and Meryl Streep and it’s set on an American farm in the 60s. Meryl Streep’s character is a house wife who is home alone looking after things while her husband and son are off at some fair. Clint is a photographer who’s passing through town taking photos of bridges in the area. I don’t want to ruin anything by telling you anything else, but please do watch it if you haven’t.

The Time Traveler’s Wife (2009)

Rachel McAdams and Eric Bana co-star in this one about Henry, a man born with an ability to time travel. You might be thinking that this one sounds A LOT like the other time travel romance in this list, ‘About Time’, but despite the fact both are about time travel and star Rachel McAdams, they are different movies. This is a memorable movie and my synopsis just won’t do it justice so you’ll have to watch it.

Ghost (1990)

There is one scene in this movie that transcends the movie itself. You know the one. It’s worth watching the entire movie just for that scene. As you get older and experience more love and loss, I think this movie gets even more emotional. Pass me the tissues!

Amelie (2001)

Amelie is an incredibly cute and clever French film. It’s rare for a foreign language film to gain popularity in English speaking countries, but this little movie did just that. The film follows the main character, Amelie who performs little acts of generosity and love as she herself falls in love in Paris.

Cinderella (2015)

The live action version of Cinderella is beautiful. Prince Charming is handsome and suitably charming, Cinderella is gorgeous and I was surprised how this movie really captured my imagination even though I had seen it a hundred times as a Disney cartoon movie as a kid.

Pride and Prejudice (2005)

This is one of those epic Jane Austin stories you just have to see at some point in your life. I grew up watching the BBC series of Colin Firth as Mr Darcy. If you haven’t seen this version and you’re a fan of this movie, it’s definitely worthy of a weekend binge at some point.

The Wedding Date (2005)

If you loved Pretty Woman, this flick is a bit of an equal-opportunity version of that story. Kat (Debra Messing) is freaking out about that fact she’s single and dateless for her sister’s wedding overseas. In a stroke of madness (or genius) she decides to hire a handsome male escort to be her date for the wedding. You can guess what happens next but it’s still incredibly entertaining.

Me Before You (2016)

This movie didn’t make much of a splash when it came out a few years ago but I was pleasantly surprised by this one. Emilia Clarke, (a.k.a Khalese from Game of Thrones), is an adorable ‘girl next door’ who ends up becoming the in-home carer for a paralysed man and things get a little tear-jerky from there.

Meet Joe Black (1998)

This movie gets a bit of flack because of Brad Pitt’s acting in the film, but I for one actually really liked it. Essentially Brad Pitt is ‘Death’ occupying the body of a regular Joe on earth. He meets Susan, the daughter of a wealthy businessman played by Anthony Hopkins and decides to spend some time on Earth seeing what’s what. A semi-twisted romance ensues and all the while you’re trying to work out what’s going on but you’re just happy watching Brad Pitt being Brad Pitt.

The Proposal (2009)

If you like Sandra Bullock and/or Ryan Reynolds, you’ll love this one. Sandra Bulllock plays Margaret, a bossy AF Editor who convinces her assistant, Andrew (Ryan Reynolds) to pretend to be her fiancé to avoid being deported to Canada. This is definitely a rom-com. Don’t expect any tear-jerking moments but it was very entertaining the first and second times I watched this one.

The Holiday (2006)

If you like the idea of escaping to another country, any film with Jude Law in it and the idea of a holiday romance, then this film will tick a lot of boxes for you. In a nutshell, two women, played by Cameron Diaz and Kate Winslet, decide to switch lives for a few weeks after swearing off men for good. They house-sit each other’s houses – one in L.A and the other in a country town in England. Cameron meets Jude and Kate meets Jack (Black) and romantic comedy gold ensues from there.

Something’s Gotta Give (2003)

I found this movie refreshing, romantic and aspirational. It’s refreshing because it’s a romantic comedy starring two mature actors who were in their 50s and 60s at the time it was made. It’s definitely a romantic story and I found it aspirational because of the setting. Most of the film takes place at a gorgeous property in the Hamptons with stunning décor in pretty much every shot.

© My Wingwoman 2019

Related articles

30 fun summer date ideas

30 fun summer date ideas

Audrey Claire, My Wingwoman Founder & CoachIt’s tough coming up with date ideas. If you’re someone who stresses about this, you’re definitely not alone. This blog will hook you up with some date options for Melbourne, but even if you’re living elsewhere, read on...

Get In Touch

I’d love to hear from you! 

Feel free to simply enquire or schedule a completely free, no-strings-attached 20 minute phone consult.

Call Audrey