Season 3: Episode 13 - Ten Sessions

Ten Sessions: Ted has ten tattoo removal sessions to win over his dermatologist Stella and get her to agree to go on a date with him. After trying gambit after gambit to break through, including being extra nice to her receptionist (Britney Spears) only to have the receptionist misconstrue Ted's friendliness as attraction, Ted finally discovers why Stella has been hesitant to get involved. Ted must decide if he really is ready for a more adult relationship, and convince Stella of the same.