1. Of a plan or idea, to seem acceptable or ideal. Sometimes used sarcastically to imply the opposite. The board of directors agrees with me that your proposal sounds like a real winner, so we are prepared to move forward with it right away. A: "Did you hear about Sarah's boneheaded plan?" B: "Yeah, it sounds like a real winner, huh? What on earth is she thinking?"

2. Of a person, to seem very well suited (to someone) in a romantic capacity. Sometimes used sarcastically to imply the opposite. A: "She just got a job with a big financial firm, she writes poetry in her spare time, and she loves anime." B: "Wow, dude, she sounds like a winner! You must be elated!" A: "Jenny's new boyfriend is an ex-con and apparently has a pretty bad drinking problem." B: "Huh. Sounds like a real winner, then."