The best way I could get this done was by flirting with him. Altough, I've never really had he respect me...lol.
Also get him gifts, where clothes that have that certain appeal (romance).
I changed my clothes often throughout the day; the boss likes that too. When she comes around change your clothes to something with a high professional look.
There's a couple things you can do: First, talk to Hugh throughout the day, stroke his ego, etc. but not when the Boss is around. If you flirt or try to get him to like you when the Boss is around, he'll be disgusted. Second, get the most expensive outfit you can afford but the outfits that Hugh likes are not always the ones that impress the Boss. Third, buy Hugh gifts, you'll get a lot of points with him for that. Fourth, invite him to the bar towards the end of the day. Hugh does his best flirting at the bar. Lingerie and gifts are required if you want things to progress with Hugh. Just a tip, being on good terms with Hugh does not mean the game will be easy to win. Mid-week, he becomes more determined to win and is tricky, regardless of what your relationship is with him.
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