This is available during the second date with Maya and can be combined with
Here is a list I made to help you get both in one run (optimally during your Maya playthrough).
For my profile I chose; Education, Arts & Culture, Partying, Music, & Libra since Maya likes the similarities in interests.
Date One
Date one complete and a huge success. Make sure to choose Maya to advance to date two.
Date Two
*** Spoiler - click to reveal ***
1. Dare
2. Accept (Achievement)
3. Eat something without using her hands
4. Truth
5. Role-play
6. What do you think of Vinny/Me
7. Another Round
8. Truth
9. Rob a Bank
Enjoy