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Really you would do that? I mean sure why not

— Harold Branley

Detailed quest

First ask Harold Branley he can be found in the equipment room of the school,Talking to him with a perception of 7 or Lady Killer/Cherchez La Femme will find out that he has a crush on someone after a speech check of 45 he will admit he does and its a scavenger after talking to the scavengers the only remaining scavenger will be Hailey Briggs(you can skip this part by talking straight to Hailey)

Telling the truth

When speaking to Hailey about the subject she will feel uncomfortable after convincing her to tell the truth she will admit she has one too with Harold Branley but she doesn't know what to do telling her a plan with a speech check of 60 will make her do all the work,Failing the speech check will get you to prepare a date with the 2

Setting up the date

(note if you pass the speech check wait outside the school till 5:00 pm)Find 2 Broc flower (Fallout: New Vegas) one Glass pitcher and Xander root (Fallout: New Vegas) and wait infront of the school till 5:00 pm the date will be successful any everyone will be happy

Quest stages

StageStatusDescription
10 Talk to Harold Branley about his crush
15 Talk to Hailey Briggs about her crush on Harold
20Quest finishedIcon checkSet and plan the date

Behind the scenes

Happy hearts day means its Valentines day