Because I keep thinking you have to use one item when you have to use another; the video and this guide are a bit different from each other. This blog entry assumes you've done Nari first, even though I restart from a certain point and date Diana first because I am dumb at writing things down while taking notes. You'll soon find out it makes more sense to date Nari first, then date Diana.
I will never live this down.
Head to the VIP lounge at Hell's Pawn and take the dismembered arm sticking out of the dark room doors. It's a rubber arm. Combine it with the jackhammer sex toy in the inventory, then go back to the gym and use your jackhammer arm on the punching bag. You'll get an Instacrap cutscene where you pass Diana's first test. Diana loves the idea of a date, and really want to let herself go, but hasn't dated in a long time. Larry offers to teach her how to date him (as only he can) in addition to helping him with his fitness plan. Unfortunately, her fitness watch gets in the way, and she tells Larry to meet her at the pier.
Head to the funfair and talk to Diana. She will now want to see if you can ring the bell on the high striker. If you click on the high striker hammer now, you'll get an Instacrap cutscene where Larry fails. If you use the lubed plunger on the high striker puck and click the hammer after that, however, you'll pass Diana's second test in yet another Instacrap cutscene. Diana considers letting herself go, but the fitness watch warns her that she has not burned enough calories in the last hour, and Diana runs back to the gym.
At the gym, talk to Diana. You'll find out that Diana's fitness watch - which is ruining her life at this point - is recharging and going through a software update. Diana asks Larry not to mess with the watch or else her settings will get messed up. She will then ask you to talk to Steven (or Phtheven) and ask for her organic protein shake. Talk to Steven and ask for the protein shake, and you'll find out he drank it. He will then mention that you will need a fresh cucumber, kale and protein, and that the smoothie will have to be soy-based, too. We already have the cucumber and the protein powder. We should have the kale from the PrunePal section of the Leisure Suite grocery, and we should already have the expired soy from the Salon Du Lezard, which we got long ago.
If you haven't gotten the beer ingredients for Lefty, bring them to him now. This will allow you to use the brewery. Open the middle washing machine and place the soy, the protein powder, the cucumber, and the kale inside. Click on the middle washing machine again to close the door, then use the thermal jug on the tap to put the shake into a container, then head back to the gym. Give the shake to Diana, and she will drink only to find out there is traces of gluten before becoming paranoid about her health.
Larry will take advantage of the situation and re-program the fitness watch, and when Pi asks him what he is doing, Larry basically tells Pi that the fitness watch is running every aspect of Diana's life to the point of misery. Pi tells Larry to program having sex with him into the fitness watch, which he does.
Diana will come back and realize that the fitness watch is ruining her life, then tells Larry it's time for their date and that it is time for Larry to show her how to enjoy life again. You should have the upstairs room to yourself due to bringing the beer ingredients to Lefty, so you should be able to take Diana somewhere private.
You'll soon be at the upstairs room at Lefty's. Larry and Diana will talk about the fitness watch. Regardless of what dialogue options, you pick, you'll get the Instacrap cutscene with Diana. The watch goes off and tells Diana to have sex with Larry, but Diana has finally had enough with the watch. Diana then thanks Larry for opening her eyes to enjoying life again, then gives him a top rating on Timber. You'll also get another achievement ("Diana.")
If you've already handed the USB stick to Anu by this point, you'll then get a cutscene at Prune Headquarters with Faith and B.J. It will soon be revealed that the PiPhone prototype ended up in Lefty's Bar after B.J. got absolutely drunk and puked in the bathroom toilet, losing the phone in the toilet in the process and endangering Prune's work. Also, Faith is the real boss of Prune, while B.J. is just the visual frontman and eye candy.
If you haven't given the USB stick to Anu, you'll get it when you do.
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