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Here's a few hints if you're still interested

1) Tell him the balloon is a sweet idea

2) Play along when he asks if you're a motivational speaker. Your motivation doesn't come cheap.

3) Be more positive when you go to the Other Side. Say that it's radical!

I've actually tried all three of those things in the same run and I got friendshiped again, I think I have to talk about his date? Possibly? Idk I'll have to test it out

Try following this play through, the romance end is reached near the end of the video!

https://www.youtube.com/watch?time_continue=721&v=p6B9X5CF6eU&feature=emb_logo