In week 6 of Helping Joe, Charlie brings in one of his female friends to show Joe first hand what she experiences when dating online or through Tinder. She also gives him feedback on his profile and advice* on what to do and not to do when messaging women. Tucker makes a lot of jokes and draws out great feedback from her. He is also a case study here for one way to tease and have fun with a woman.
*She was good at knowing what she wanted but bad at extrapolating this across women in general. Most of what she said was specific to her. It's better to ask a woman what she personally wants and listen, not ask her what all women want because she will project her preferences onto all women and give you bad advice.