Cupid - Season 1 Episode 7 : Pick-Up Schticks 1999

Trevor is growing desperate. Caught between his desire to return home and his jealousy at seeing Claire having a serious relationship with Alex, he makes his first mistakes as a love counselor. On one side, he encourages a man to use a ""sure score"" pick-up technique that gets him the woman he wants but leaves him distressed and disgusted with himself for he feels he cannot be with a woman that would fall for such a trick. On the other end of the tunnel, his friend and roommate Champ is starting a new relationship and Trevor can't help but intervene - and in ways that pushes the woman away rather than bring her closer. And somewhere in the middle, Trevor himself is caught up in a strange relationship with Helen Davis, a woman he met at the bar. They're both attracted to each other, but Trevor tells Champ he can't have a relationship with a mortal, or he'll lose his immortality. And yet, he might just be desperate enough to not want it anymore...