Edit - Turns out I had a brain fart and swapped "Flora's Hug" and "Flora's Embrace" in my head, sorry about that... So for "Flora's Embrace" which is acquired during the Season 2 Quest "Paint the Town" you will want to go down both the Jacklyn and Flora routes, trying to be as good to Flora as possible as well as pushing things forward with Jacklyn. It would also help to go a little ways down Lindsey's route too.
"Chili Con Carnal Sin"
"Oxygen for Oxymoron"
"Hide and Seek"
"Tiny Thirsty Tree"
"Fully Booked" - When the Beaver makes off with the Makeshift Easel go after it and get the body.
"Art Through Suffering" - Quest Jacklyn and ask to join her class, just don't say art sucks. Once ready to paint Use the Beaver Carcass as a paint brush and Jacklyn will be impressed, giving you her number.
"Punked" - Quest Flora while she's in the Kitchen to start this Quest.
"A Short Fuse" - If you have at least 1 Lust with Jacklyn at the end of this Quest you can convince her to become the model.
"The Statement" - Have dinner with Jacklyn, then go check your closet. Talk to Flora, tell her you are all bad liars then go with Jacklyn.
"King of Sweets" - Quest the Guard's Booth then go steal Doughnuts from the Cafeteria and tell Jacklyn you're doing an art project.
Finish Season 1
"Fall in Newfall"
"Big Witch Energy"
"Suitable Romance" - Get a suit and when Flora confronts you about it tell her that you and Jacklyn are just friends going to see some art. You will need at least 10 Lust with Flora to do this.
"Paint the Town" - Tell Flora you're sorry she wasn't invited, then at the end of the "date" choose to go after Flora. Try to enter the Bathroom and ask Flora to let you in. Once inside tell her that nothing happened. You will need at least 25 Love with Flora to make these choices.
Sorry for the shitty/half-assed quality of this, it's 2:52am and I'm barely awake. You're smart, you can figure it out without me handholding. :) Good luck!