First I love you

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Ben:
You and Ben had said I love you to each other for the first time on Christmas Eve.

Gil:
You and Gil first I love you happened on July 4th

Carlos:
Carlos took you on walk before saying I love you to you for the first time and you said it back

Jay:
Jay first said I love you to you when you were able to join him at Auradon then you told him the same.

Doug:
You and Doug first said I love you to each other when you made 3 months

Chad:
Chad and you both said I love you for the first time at a party

Harry:
You told Harry you loved him after dating for a few weeks but he didn't say it back until a few days later.

KlaudiaKlauR5 thank you for the idea

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