|Nate and Serena|
|First Met:||Before "Pilot"|
|Started Dating:||3x13–3x22 (2010; 4.5 months)|
|Status:||Fling; Exes; Close friends|
Serena and Nate have been friend since early childhood. Nate lost his virginity to Serena shortly prior to the show beginning, at the Sheppard Wedding, shown in the series premiere. Throughout the series, they continue being best friends, date in Season 3, and break up towards the end of the same season. Though it took sometime to reconcile, Nate and Serena remain best friends for the rest of the show. In the finale, Nate attended Dan and Serena's wedding.
In the Gossip Girl novel series, Serena and Nate are on-again, off-again. They lose their virginity to each other in the series prequel, It Had To Be You, during the summer before Serena leaves for boarding school. Once Serena returns, their antics often lead to the break-ups of Blair and Nate. Serena realizes her love for Nate at various points in the series. One of the main reasons stopping their relationship is that their best friend, Blair Waldorf, is also in love with Nate. In the final book, I Will Always Love You, Nate chooses Blair in Part I and then Serena in Part II. In the end, Nate ends up with neither, and Blair and Serena go off together as best friends on vacation.
In the television adaption, Serena is the reason Nate and Blair break up; Serena and Nate slept together at the Sheppard wedding during their sophomore year before the start of Season 1 as juniors. They finally get together in Season 3, but towards the end of the season, experience bumps in their relationship and break up.
In the 1st season, when Serena returns, Nate hopes to give their relationship a real chance. But Serena refuses, saying ,"I didn't come back for you. Look, Blair's my best friend, and you're her boyfriend, and she loves you." However, Serena still agrees to meet up with Nate to talk with about their current situation.
After Nate promises Blair that he will never see or talk to Serena again, he gives Serena a cold shoulder during Ivy Week. Throughout the season, their friendship mends. Serena dates Dan and Nate dates Vanessa. In the end of season 1, they are seen together as friends welcoming summer.
The 2nd season opens with Nate and Serena pretending to date and sharing a very public kiss. As the season progresses, both Nate and Serena date other people. Serena dates Dan, Aaron, and Gabriel. Nate dates Catherine, a married older woman, during the summer, but they soon break up. After they kiss at the white party. Nate also dates Vanessa, but the pair break up due to incompatibility and differences in their interests. Towards the end of the season, Nate dates Blair, but they agree to end their relationship by the time they graduate. Throughout the season, Nate and Serena remain friends who are always there for each other.
Serena and Nate get together in season 3. Nate tells Serena that he has been crazy about her all these years since the Shepherd wedding.They start becoming closer as Serena begins an affair with Nate's married cousin, Tripp Van der Bilt. In episode 12, Nate becomes Serena's hero and saves her from a terrible car accident caused by Tripp. This happened because Serena ran away with Tripp in the previous episode. They begin 'officially' dating from the episode 'The Hurt Locket'. In the following episodes, they finally get their chance at a happy romantic relationship and Gossip Girl dubs them the "Golden Couple" as they seem perfectly happy with each other. Jenny Humphrey tries to get between them but fails. However, issues rise once more between Nate and Serena towards the end of the season involving Serena's dad and Dan Humphrey. In the season's finale, Serena ends her relationship with Nate.
In season 4, Serena and Nate aren't romantically involved. It opens with Nate still heartbroken over his break-up with Serena. He and Serena are on speaking terms but not super-friendly. Nate starts dating Juliet, a girl secretly obsessed with taking Serena down, and this causes jealousy on Serena's part. However, Nate soon decides to win Serena back. Serena ends up in a situation where she needs to choose between Nate and Dan. Nate still cares for her but is put off when Juliet pretends to be Serena and kisses both Nate and Dan. Nate clarifies that this is typical Serena behavior and that he is not going to let her pull him back in ever again. Dan disagrees.
In rehab, Serena admits to Dan that she had picked him, that he was the only one she came to kiss.
In season 5, Nate and Serena's romantic prospects officially come to an end. On the day of Blair's wedding, Nate tells Dan that he has never had an honest relationship and that the only girls he has chased have been wrong for him.
On the same day, Serena professes her eternal love for Dan Humphrey and tells him that she has always loved him and he is the only one she will always love.
In the finale, Nate is present while Serena marries Dan Humphrey.