I haven´t reach Steve yet. And Biff hasn't asked me that. So far in the clothing store i was only able to do the housewife outfit for Bardie and Eric. I have finished right about now the fourth photoshoot and only now reached level 2 with Alex. I´m already able to do the Melanie photoshoot. It seems i did one or two things out of order concerning the clothing store, but nothing impactful thankfully.The clothing shop path is not missable, the red dress is a requirement to continue some paths and begin others. You may have run into one of the bottlenecks in the game (as stan5851 suggested a few posts up). Had Steve visited Betty and Ralph's home yet in your playthrough?
Also don't get to hung up on completing each photo shoot twice. You only need the photographer to get to level 2 eventually for him to have enough balls to go further If you choose the middle and low angles each shoot you won't need to repeat them. The event list is a little deceiving on this point.
When you were stuck for the 15 days was Biff suggesting that Monica wear some better clothes to work?
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