Lori digs deep with new client 32-year-old Manhattan bartender, Dana Tompkins, to uncover exactly why he's so picky in love. He's comparing everyone to his ex-girlfriend. Believing everyone has more than one soulmate, Lori sets Dana up on his first blind date with someone he would never expect to see if he's truly ready to open himself up again. Lori's other client, 29-year-old Jesse Osher, suffers from serious confidence issues in dating. After a manscaping session and some one-on-one coaching Lori-style, Jesse heads out on his first date groomed and ready for love.