Your date

Five rounds. One duet.

Take turns choosing songs for each other and end the night with a duet and a final dare.

Head to a karaoke night or use a karaoke app or videos at home; a microphone is optional. Start with a song each of you feels comfortable singing. Next, choose a song for each other, then pick something wildly outside your usual style. Sing a duet together, and finish with one final challenge song each. Either person gets one no-questions-asked veto. Cheer each other on and award your own titles for best performance and biggest surprise.