Do you mean the regular couch massage or the one with the alcoholic candy? I've done several months worth of perfect candy massages and never triggered the massage for Lisa. Didn't try going back to the normal couch massage without the candy.Have you read this.
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About once every 2-4 days, if you Wake up later than Lisa, she sees Max's boner. This should happen a certain number of times and eventually lead to her agreeing to learn adult tricks from Max. To open a massage for Lisa, you first need to go the entire distance several times in a massage with Alice at the TV, and she will brag to Lisa about what Max can do.