Gossip Girl was a huge hit throughout the entire six seasons — it had tons of drama, scheming, insane wealth and like most American teen dramas, a constant interchange of relationships and romance. Serena van der Woodsen was the leading lady of the show and as the constant ‘damsel in distress,’ she seemed to have a revolving door of boyfriends throughout the entire franchise. We all knew that Dan Humphrey and her would end up together, but of course, she had to date many, many frogs along the way before she realized this. Here’s a definitive ranking of Serena’s top 7 worst boyfriends on Gossip Girl!
7. Nate Archibald
We loved the character of Nate Archibald, but we weren’t so hot on the relationship between him and Serena. Right from the get-go it started off on a bad foot when these two got together behind Blair’s back. That hook up looked bad not only on Nate, but also on Serena. We admit they had a little bit of chemistry, but it was pretty clear these two were better as friends. The entire relationship was physical and never really reached a deeper level and sometimes seemed a little forced. Not to mention, Nate has the worst taste in women…he always seems to make the wrong choices and pick the wrong girls. He just can’t catch a break! Luckily, fate stepped in and the timing never panned out for them to actually make it as a couple. Whenever they tried, one of them would still be reeling from an ex, or couldn’t commit to a relationship or was still involved with someone else.© The CW / Courtesy Everett Collection