While I did find it entertaining, Gossip Girl has its flaws. But First, let us go to its wins and then talk about its sins:

[spoiler]
The Wins

The Shows starts fine to good. Its characters are interesting and Dan Humphrey serves as the chain that connects the audience with the plot. This is basically the first season introducing the main plot, where a low-medium class boy from Brooklyn ends up in the world of Upper East Side (as a foreign this means nothing, but the show explains it nicely). This high-class society has a "villain" in the website Gossip Girl that releases secrets and news in blog form. The first season, besides setting the plot and presenting the characters, makes the plot interesting enough to follow and relatable enough in the hands of Dan, Jenny, Vanessa, and Rufus. It shows that even Rufus have some secrets, some people are not what they seemed, but the plot does make sense.

All the way to the third or four season things are good to really nice. There are more plots, more interesting characters like Georgina. Some romances you start wanting to end up together are form and then ends miserably, though not unbelievably and not logically.

The last few seasons like the fifth and sixth manages to get very few wins. The only I found really worth noting is making Blair more sympathetic to the viewer. The last episode is actually nice, though it has many sins in it that I'm going to write about.

The Sins
The first sin is related to this type of TV show, or in other words, its genre. More specifically the tsunami of drama it happens to the main cast of the show. We see it in Grey's Anatomy, though more emotionally presented, we see it in Supernatural with its resurrect Dean to resurrect Sam to resurrect Dean to resurrect sam.... and so on. Gossip Girl has something similar, it has its drama focused on the inability of the characters to actually sit down and talk to each other. The repetition of secrets and "I can't tell you right now" appears to be needed in the time a plot is happening, but if you pay attention, one may see that the whole thing happened because this one person did something stupid like plotting a ridiculous plan instead of talking to people. I mean, if you have a secret and it relates to your ex, it doesn't matter if it is a secret while you are in a relation.

Another sin is the unbelievable shit people do here and get out of it as if nothing happened or the character is just hated now. For example, Jenny gets drugged and left to be raped by some guys in an unknown place, it doesn't happen because Nate saves the day and rescues her. This is fine, but have you heard of something called "CRIME"? If someone breaks the law he/she deserves to be locked up, not just "forgive or just forget".

And to end this long superficial analysis with what I remember now of the show: Dan Humphrey becomes evil than good and reveals he is Gossip Girl. To be honest, here, the only person I actually cared about in the begging of the show was the Humphreys and Vanessa with some kind of niceness towards Selina (which becomes evil basically, when she deceives Dan and tapes a sex tape to punish Blair (WTF?)). To turn him evil would have made some sense if it started in the first season while turning other characters more likable (yes, even more, likable than Chuck or Blair did, they still did some pretty shitty stuff towards the end). The fact that Dan is Gossip Girl feels more like the writers wrote the show with the possibility of anyone being Gossip Girl, and if someone had a pretty good shot at it, they would have revealed it was another person. While it doesn't make sense of Dan being Gossip Girl, the fact is that during the first seasons I kind see some things that don't make much sense, if I'm not remembering correctly, wasn't Gossip Girl who got in the way sometimes of Dan's relationships? To be honest I don't remember, even though I just marathoned it. [/spoiler]