Nate Archibald Relationships

Jordan Steele

Hookup "New Haven Can Wait"

Serena van der Woodsen

Start up: Before Pilot (One Night Stand) Nate finally acted on his feelings for her.
Confirmed In: Pilot (101)

Blair Waldorf

First Relationship:
Start Up: Before Pilot (101)
Broke Up: Victor, Victrola (107)
Reason: Blair confronts Nate about his confession to 'Serena'.

Second Relationship:
Start Up: Hi, Society (110)
Broke Up: School Lies (112)
Reason: Chuck threatens to tell Nate about his and Blair's relationship if she continues seeing him.

Third Relationship:
Start Up: School Lies (112)
Broke Up: The Thin Line Between Chuck and Nate (113)
Reason: Nate finds out Blair slept with Chuck.

Fourth Relationship:
Start Up: Remains of the J (220)
Broke Up: Seder Anything (221)
Reason: Blair lied to Nate about his grandfather.

Fifth Relationship:
Start Up: Seder Anything(221)
Broke Up: Valley Girls (224)
Reason: Blair felt their relationship is already just a high school memory.

Vanessa Abrams

First Relationship:
Start Up: Desperately Seeking Serena (115)
Broke Up: Much "I Do" About Nothing (118)
Reason: Nate wasn't ready to be in a relationship.

Second Relationship:
Start Up: It's A Wonderful Lie (212)
Broke Up: Remains of the J (220)
Reason: Because his feelings were over for Vanessa and he relaized he wants to be with Blair.

Catherine Mason

Start Up: Summer, Kind Of Wonderful (201)
Broke Up: The Ex Files (204)
Reason: He found out about her secret relationship with her step-son, Marcus.

Jenny Humphrey

Start Up: Pret-a-Poor-J (208)
Broke Up: The Magnificent Archibalds (211)
Reason: Nate and Jenny haven't spoken to one another in weeks.