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You do have to plant the flower. In order to be able to give it to him though, you have to do the following: get a kiss from the drunk lady in the lounge. Kiss the flower. It should open its "mouth", if memory serves. If you used the janitor's ID to get a drink from the bartender, give the drink to the flower (and if you don't have it, make sure to get it!). She'll smile for you. Use the toothbrush on her, and she'll blossom. Use the hand, grab the lily, and you'll be good to go!
Also: get another kiss from the lady in the lounge and use it on Habit after you've punched him once. I'm not sure if it's required or not, but it provides a nice transition into you giving him the flower.
Not sure who the ducky belongs to though, I'm afraid! I'm hoping to check that out as well. :> The other achievements are a mystery to me too, but I'm gonna have a go at it tomorrow after I get some sleep.
Re: True Anarchist, apparently I already got that achievement and didn't realize it until just now lmao! You get it from our friend with the pickle jar—you have to hit him with it until it cracks open and gets pickle juice everywhere, I believe.