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The Carrie Diaries – 2.01 –Win Some Lose Some – Advanced Review: ‘Life is like a game of chess…’

“Life is like a game of chess.
To win you have to make a move.
Knowing which move to make comes with IN-SIGHT
and knowledge, and by learning the lessons that are
accumulated along the way.
We become each and every piece within the game called life!”

- Allan Rufus, The Master's Sacred Knowledge

Title: Win Some, Lose Some
Written By: Amy B. Harris
Directed By: Andy Wolk

Synopsis: It’s the summer of 1985, and, for the first time, 17-year-old Carrie Bradshaw (AnnaSophia Robb) can call Manhattan home. After her boyfriend Sebastian (Austin Butler) and best friend Maggie (Katie Findlay) betrayed her, Carrie is happy to accept the offer to spend the summer living in the downtown loft apartment of her Interview magazine boss Larissa (Freema Agyeman). But as summer turns to fall and Carrie heads into her senior year, she and her friends and family discover that letting go of old loves and embracing new dreams comes with some tough new realities but also incredible new opportunities.

When it was announced that The Carrie Diaries would be getting a second season, I was happy. Maybe a tad bit flummoxed due to the ratings but happy nonetheless. It would have been a shame to leave fans wondering what happened next after a finale like the first season had. So when the opportunity presented itself to receive an advanced look at the season 2 opener, I jumped on it.

I should have probably prefaced this in the beginning but I’m a casual fan of the show. It lured me in because I loved the prequel book which the show is based on. Also I heart the lovely and talented AnnaSophia Robb to pieces. The Carrie Diaries is not one of the shows that I seek out spoilers for. I like to just sit back, be surprised and enjoy the ride. I couldn’t avoid the biggest spoiler of season 2 however which was the character introduction of Samantha Jones.
Samantha Jones is not my personal favorite character in ‘Sex and the City’ but she is a fan favorite in general. In the pictures the actress, Lindsey Gort, looks so much like a young Kim Cattrall it was a little uncanny. But I think something gets a little lost on the little screen unfortunately.

I find the show to be most delightful when it focuses on Carrie’s internship in New York, the adventures that ensue from her job and her relationships with Walt and Sebastian. Carrie’s other friends are not that interesting and her family time absolutely bores me to tears. I guess I wasn’t the only one because in the season 2 opener a few things have been retooled a bit and the main focus is on Carrie’s summer adventures in The City where she is loft sitting for Larissa.

So let me catch you up with where the characters are at the beginning of season 2…


Carrie is still nursing her wounded heart and is avidly avoiding both Maggie and Sebastian by avoiding Castlebury as much as possible. She has thrown herself into her summer internship. Which has the perks of partying at all of the hot spots in mid-80’s Manhattan and a stylish loft provided by Larissa. She has a new ‘do and a seemingly new attitude. While Carrie does indeed lose something very near and dear to her in this episode she gains something that is much more needed at this particular time in her life.


Walt has a guy in his life that he can’t be with until he’s legal so he just going to look at all the hot guys his eyes can handle. He seems very worried about the whole town whispering about him and his sexuality. Much like Carrie, he too is hiding out in the city avoiding things. His friendship with Donna has grown leaps and bounds. Donna keeps him in abreast of what’s happening back in Castlebury and he in turn tries his best to not inform Carrie.


Sebastian has been avoiding the country club because Maggie is working there. Sebastian is really upset with himself for kissing Maggie. He is also quite remorseful for outing Walt. He is still holding out hope that he and Carrie might still have a chance of working things out. It seems as though he spent his whole summer pining for Carrie.


Donna may seem like that same old mean girl mold. But she just wants to have fun and being bitchy to people is her way of having fun. She does have a soft spot though she doesn’t like to let it show. She’s spent her summer at the country club on the lookout for scandals and juicy tidbits to gossip about. She’s really coming into her own as a young woman. I love that show she knows what she wants and how to get as well as not being afraid to speak her mind. She also doesn’t do apologies. She has great insight and I sense she dumbs herself down a bit. Hopefully, a little more time with her cousin Samantha will fix that.


Mouse is having fun with her geek boyfriend. Her parents have taken to him like a fish to water. Her and West have decided to take SAT prep courses as well some high level math class to beef up their course loads. Yes, to Mouse that is fun. Mouse is also avoiding Maggie like the plague because of what she did to Carrie. Carrie convinces her to the 4th of July barbeque at the country club and to take West and have a good time.


Maggie has had a rough summer and found out that if she wants to go to college she’s going to have to pay for it herself. Thus her mighty need for a job at a fancy place with fancy people who should tip well. Maggie needs to stop playing the victim though. Even with her implied neglectful parents, I’ve never felt sympathy towards the character at all. She’s way too needy, clingy and pouty. Time for this character to really grow up or move away.

Samantha Jones

When we meet her, she is the keeper of the cool aka a bouncer. She’s definitely into the 80’s music scene and the bar that she works at is THE place to be. We can see that oh so familiar sassy, independent and confident streak but there are a lot of hard life lessons to come that will ultimately shape Samantha into what she becomes later on. Right now, she seems very lost and drowning in the real world while desperately seeking to find her place in it. At least she’s found her anchor in Carrie so now she can settle down and begin to blossom.

The Rest of the Bradshaw Clan

Mr. Bradshaw was clueless as ever until Carrie let it slip that Dorrit had a guy in her life. Now he’s on a mission to keep close tabs on Dorrit and her boyfriend. He seems to like Miller.

Dorrit has been sneaking around with Miller and using her best friend as her cover to be alone with him. Now that her relationship with Miller is out in the open and Miller seems to like her Dad I have a feeling her rebellious streak is going to come rearing back, if one of the last scenes is any indicator.

Favorite Moments

• Carrie and Samantha walking down the street together looking very stylish.
• An awkward Bradshaw family brunch.
• Carrie’s opening dream sequence.
• Sebastian tucking in Carrie after a rough night.

Favorite Lines

• Maggie: It takes to tango.
Donna: Not when you’re involved. You just drag the poor soul along.
• Carrie (to Mouse): Well, apparently “in love” Dorrit is just as sullen with my dad as she ever was.
• Carrie: Sometimes you have to sacrifice something valuable in order to win.
• Carrie: I don’t have time for regrets, only fun.

Favorite Scenes

• The introduction of Sam(antha) Jones.
• Carrie and Samantha breaking into Larissa’s loft.
• The arrival of Donna at the loft with Sebastian in tow.
• Dorrit’s rebellious streak returns.
• Walt and Sebastian get to talk it out.

The Standout Character

While the beginning of last season had me all set to hate Donna LaDonna (Chloe Bridges) for life but by the end of the first season, I was on a hate to love her basis. During this episode, it became official I just flat out love her. She’s snarky, sassy and very pragmatic (I guess it runs in the family?). As well as stylish and not afraid to go after what she wants. Best of all she breaks the awkward silences and lightens the mood. Love to hate her or hate to love her you have got to admit Chloe Bridges is a scene stealer.

Best Old School NYC mentions: Limelight, Area and Danceteria

Most Out of Place Pop Culture Mention: Charlie’s Angels

Cool News – Though the actor has not been cast yet, word on the street is that the character of Standford Blatch will be introduced this season as well. I’m sure we here at Spoiler TV will keep you abreast of the situation.

Grade: B-

Don’t forget to connect with the show!
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Twitter - @cwtcd

Season 2 of The Carrie Diaries premieres Friday, October 25, 2013 on The CW at 8 PM/7 PM Central.

Feel free to sound off and/or ask me general questions about the episode in the comments below.

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