Love, Random

My Top 10 Favorite Chick Flicks

We all have movies that we can watch over and over again and I’ve always been a hopeless romantic, so therefore I am a sucker for “chick flicks”. Chick flicks are always predictable and I’m usually in tears at some point in the movie, but they are in no way indicative of real life. I think that’s why they’re so charming though especially when you’re single. Singledom can be a depressing time, but romantic movies always offer a little glimmer of hope even in the darkest of times. Thankfully I am no longer a singleton and my Prince Charming is way better than fiction, but I still need chick flicks in my life.

I’ve compiled (in no particular order) a Top Ten list of my favorite chick flicks:

1. The Wedding Date (2005) starring Debra Messing, Dermot Mulroney

Plot: Kat Ellis (Debra Messing) is a single New Yorker who returns to her parents’ house in London to be the maid of honor at her younger half-sister Amy’s (Amy Adams) wedding. The best man is none other than her former fiancé, who unexpectedly dumped her two years ago. Anxious about confronting him and eager to impress him, she hires suave escort Nick Mercer (Dermot Mulroney) to pose as her boyfriend. – Wikipedia

My thoughts: I’ve lost count of the number of times I’ve seen this movie. It’s probably an embarrassingly high number. I can’t help it though because Dermot Mulroney and Debra Messing have amazing on-screen chemistry. But seriously, who hires and escort to accompany them to a wedding?

Favorite Quote(s):

“I’d rather fight with you than make love with anyone else.” – Nick Mercer

“You’re like the Yoda of escorts. Getting you on the phone was harder than getting into college.” – Kat to Nick

2. The Holiday (2006) – starring Cameron Diaz, Kate Winslet, Jude Law and Jack Black

Plot: Two women, each troubled with guy problems swap homes in each other’s countries, where they each meet a local guy and fall in love.

My thoughts: Two words – Jude Law. So dreamy and so British. I have a thing for British men and his character is a sappy romantic who weeps during a good book. Perfection. Jack Black is not my ideal movie love interest, but somehow in this movie he is just that. He’s equal parts nerdy and charming, much like my husband.

Favorite Quote(s):

“Iris, if you were a melody… I used only the good notes.” – Miles

“I have another scenario for you – I’m in love with you. I apologize for the blunt delivery, but as problematic as this fact may be, I’m in love… with YOU.” – Graham

3. P.S. I Love You (2007) – starring Hilary Swank, Gerard Butler and Harry Connick, Jr.

Plot: A grieving widow finds her husband’s warmth radiating from the afterlife when she discovers that he left her a series of tasks to be revealed in ten monthly messages and designed to help her overcome her sorrow while gradually making the transition into a new life. – Rotten Tomatoes

My thoughts: Gerard Butler has been making me swoon ever since I saw him for the first time in Lara Croft Tomb Raider: The Cradle of Life.

No one likes to think of their spouse dying, but wouldn’t it be such an enormous comfort if they had somehow managed to leave you 10 amazingly well crafted letters designed to arrive at just the right moments during the grieving process? In the real world most people don’t get the luxury or planning these things out. Even still this movie is an amazing tale of the enormous amount of love these two characters have for each other and no matter how many times I watch it I always, always ugly cry.

Favorite Quote(s):

“What do you want? I know what I want, cause I’m holding it in my hands.” – Gerry to Holly

“Every morning I still wake up and the first thing I want to do is to see your face.” – Gerry to Holly

4. Notting Hill (1999) – starring Julia Roberts and Hugh Grant

Plot: Can a beautiful and internationally famous American actress find happiness with a frumpy British bookstore clerk? She can — at least for a while, it seems — in Notting Hill. William Thacker (played by Hugh Grant) is a bookseller at a shop in the Notting Hill district in West London, who shares a house with an eccentric Welsh friend, Spike (Rhys Ifans). One day, William is minding the store when in strolls Anna Scott (Julia Roberts), a lovely and well-known actress from the United States who is in London working on a film. She buys a book from William, and she is polite and charming in the way a famous actress would be with a star-struck sales clerk….read more at Rotten Tomatoes

My thoughts: In my opinion Julia Roberts is the queen of romantic comedies. She’s funny, quirky and I think she’s beautiful despite what some people say about her looks. Hugh Grant is much like he is in most of the movies he stars – cute, instantly likeable, somewhat clumsy and has just enough sex appeal for me to be drawn to him. Hugh and Julia have great chemistry and make a sort of odd, but loveable on-screen couple.

Favorite Quote(s):

“And don’t forget… I’m also just a girl, standing in front of a boy, asking him to love her.” – Anna to William

5. Pride and Prejudice (2005) – starring Keira Knightley and Matthew MacFadyen

Plot: The Bennets (Brenda Blethyn and Donald Sutherland) are the parents of five daughters near the close of the 18th century. Comfortable within their means but well short of rich, Mr. and Mrs. Bennet are looking for suitable husbands for their girls, and they are encouraged to learn that an eligible young bachelor from a wealthy family, Charles Bingley (Simon Woods), has moved into a nearby estate. Eager to see if a match can be made, the Bennets bring their daughters Elizabeth (Keira Knightley) and Jane (Rosamund Pike) to a ball thrown by their new neighbor to see if sparks will fly….read more at Rotten Tomatoes

My thoughts: I will stop what I’m doing anytime, anywhere to watch this movie if it’s on. Pride and Prejudice is my favorite Jane Austen novel and I prefer this adaptation to the Colin Firth version. I know, shocking right? Matthew MacFadyen is a dream to watch on-screen and is one of my favorite British actors. His portrayal of Mr. Darcy melts me and I love the character of Elizabeth. She is such a free spirit, intelligent and refuses to settle in regards to love. The love story of Mr. Darcy and Elizabeth Bennet is one of my all time favorites.

Favorite Quote(s):

“I will have to tell you: you have bewitched me, body and soul, and I love, I love, I love you. I never wish to be parted from you from this day on.” – Mr. Darcy to Elizabeth

6. Pretty Woman (1990) starring Richard Gere and Julia Roberts

Plot: Edward is a rich and sophisticated businessman who specializes in corporate raiding – buying up businesses to break them up and sell them off in pieces. Vivian is a Los Angeles prostitute struggling with her lifestyle and a need to pay the rent. On a business trip to Los Angeles, Edward hires Vivian to be his girlfriend for a week while he traverses the local social circles. Love and various social complications invade their tidy arrangement and have the pair wondering if this Cinderella-story could have a happy ending. – Rotten Tomatoes

My thoughts: This is back when Richard Gere was still hot. Who wouldn’t want an older, salt and pepper haired, rich businessman to offer them a few thousand dollars for a week of your time and then ultimately be your happily ever after? Yes, I know it’s too good to be true, but how cute is Julia Roberts in the bathtub singing Prince songs? Super damn cute.

Favorite Quote(s):

Edward Lewis: So what happens after he climbs up and rescues her? Vivian: She rescues him right back.

7. When Harry Met Sally (1989) – starring Meg Ryan, Billy Crystal and Carrie Fisher

Plot: Does sex make it impossible for men and women to be true friends? This romantic comedy chronicles this dilemma through the eleven year relationship between Harry and Sally who meet in college, then pursue their own lives until they reconnect ten years later. – Rotten Tomatoes

My thoughts: Meg Ryan is just the cutest. I love her in almost everything she’s been in and Billy Crystal is also one of those guys I wouldn’t normally consider as a love interest, but it’s his humor that makes him interesting. I’m not sure if it’s possible in all male/female friendships to just be friends without sex getting in the way, but it’s worked between me and my best guy friend for almost 5 years. The whole “too much pepper on my paprikash” scene is too adorable for words and Harry’s speech at the end of the movie still makes me cry after all these years.

Favorite Quote(s):

“I love that you get cold when it’s 71 degrees out. I love that it takes you an hour and a half to order a sandwich. I love that you get a little crinkle above your nose when you’re looking at me like I’m nuts. I love that after I spend the day with you, I can still smell your perfume on my clothes. And I love that you are the last person I want to talk to before I go to sleep at night. And it’s not because I’m lonely, and it’s not because it’s New Year’s Eve. I came here tonight because when you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.” – Harry to Sally (THIS! This makes the whole entire movie worthwhile.)

8. Love Actually (2003) – starring Hugh Grant, Colin Firth, Emma Thompson, Keira Knightley, Alan Rickman and many others

Plot: All of London is in love — or longing to be. Love Actually involves more than a dozen main characters, each weaving his or her way into another’s heart over the course of one particularly eventful Christmas. The seemingly perfect wedding of Juliet (Keira Knightley) and Peter (Chiwetel Ejiofor) brings many of the principals together, including heartsick best man Mark (Andrew Lincoln), who harbors a very unrequited crush on Juliet….read more at Rotten Tomatoes

My thoughts: I don’t even know where to begin with this one. There are so many amazing actors in this movie that it’s hard to even pick out my favorite part. I love how all of the characters are connected in some way but I really wish there was more closure with Alan Rickman and Emma Thompson’s characters. He sort of cheats on her, not physically, but emotionally and I felt that the writers left us hanging a bit too much in the end. Colin Firth’s character is definitely a highlight for me. His character Jamie falls in love with his Portuguese housekeeper Aurelia who doesn’t speak English. When he realizes he’s in love with her he begins to learn Portuguese and eventually goes to Frances and proposes to her in her language in front of her family and everyone in the restaurant where she works. Super romantic, right?!

Favorite Quote(s):

[In Portuguese] Beautiful Aurelia, I’ve come here with a view of asking you to marriage me. I know I seems an insane person – because I hardly knows you – but sometimes things are so transparency, they don’t need evidential proof. And I will inhabit here, or you can inhabit with me in England. – Jamie to Aurelia

9. Bridget Jones’ Diary (2001) – starring Hugh Grant, Colin Firth and Renee Zellweger

Plot: This romantic comedy follows Bridget (Renee Zellweger), a post-feminist, thirty-something British woman who has a penchant for alcoholic binges, smoking, and an inability to control her weight. While trying to keep these things in check and also deal with her job in publishing, she visits her parents for a Christmas party. They try to set her up with Mark (Colin Firth), the visiting son of one of their neighbors. Snubbed by Mark, she instead falls for her boss Daniel (Hugh Grant), a dashing lothario who begins to send her suggestive e-mails that soon lead to a dinner date proposition. Daniel reveals that he and Mark attended college together, during which time Mark had an affair with his fiancée. When Bridget finds Daniel cavorting with an American colleague, she decides to change her life with a new job as a TV presenter. At a dinner party, she bumps into Mark again, who expresses his affection for her; when Daniel claims he wants Bridget back, the two fight over who deserves her affections the most. – Rotten Tomatoes

My thoughts: Hugh Grant and Colin Firth again. I told you I love British men. This was my go to movie back in my single days and is why I used to journal and part of the reason I started a blog. I related to Bridget so much. She’s quirky, neurotic, awkward and has extremely low self-esteem. All qualities I possessed as a single girl and if I’m being honest I’m still very much like Bridget in a lot of ways.

Favorite Quote(s):

“I like you, very much. Just as you are.” – Mark Darcy

“It is a truth universally acknowledged that when one part of your life starts going okay, another falls spectacularly to pieces.” – Bridget Jones

10. Catch and Release (2007) starring Jennifer Garner, Timothy Olyphant, Juliette Lewis and Kevin Smith

Plot: After the sudden death of her fiancé, Gray Wheeler finds comfort in the company of his friends: lighthearted and comic Sam, hyper-responsible Dennis, and, oddly enough, his old childhood buddy Fritz, an irresponsible playboy whom she’d previously pegged as one of the least reliable people in the world. As secrets about her supposedly perfect fiancé emerge, Gray comes to see new sides of the man she thought she knew, and at the same time, finds herself drawn to the last man she ever expected to fall for. – IMDB

My thoughts: I’ll be honest. The main reason I love this movie is because of Kevin Smith. His character, Sam, so endearing and sweet. I’ve been a Kevin Smith fan for many years and it was awesome to see him in a completely different light. He is literally the best part of the movie – sweet, funny and sincere as Sam, he steals every scene he’s in. I love his movies, but I would even go so far as to say I almost like him as an actor better.

Favorite Quote(s):

Sadly, I don’t think there are any real memorable quotes from this movie, because honestly, it’s kind of forgettable outside of Kevin Smith’s performance. But don’t let that dissuade you….give it a watch.


Gosh, I commend you if you’ve made it this far. This was a long post! Honestly, it was way more involved than I had originally intended it to be, but once I got started I just kept going and going. I hope you’ll check out some of the movies above if you haven’t seen them or maybe they’re already some of your favorites too! Either way, thanks for reading about some of my all time favorite romantic movies. Whether you’re single or taken, chick flicks help to inspire us when we’re feeling a little lost or they help keep the romance alive when we’re blissfully in love.

Happy Wednesday!

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  • Reply Laura

    Oh my goodness, I love this list!! I have so many favorites on here. I think my top two (no three!!) are Love Actually, When Harry Met Sally, and The Holiday. Great list!

    June 5, 2017 at 8:08 pm
    • Reply thatmrsmiller

      It’s so cool that you love The Holiday! I’ve never met anyone else that said it’s one of their favorites!

      June 5, 2017 at 9:09 pm

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