Wrap up the "Reunions" quest to pop this one, it starts after you've finished "Unlikely Valentine".
Details contain a lot of spoilers, proceed at your own risk.
Fallout 4 can be a bit buggy in general so always SAVE OFTEN.
If you have any info you feel should be added or if i remembered something wrong, dont hesitate to comment and i will look into it.
Also, thanks to all who contributed!