It often implies an attempt at foreseeing success in things like investments, sports, or contests.

Success Prediction

'Picking a winner' is frequently used metaphorically and doesn't always involve an actual choice.

Not Literal

This phrase can associate with gambling, where choosing the winning person or thing is literal.

Highlights the chooser's personal satisfaction with their selection, especially in relationships or lifestyle.

Use it to suggest a comparison, indicating that the chosen option is better than the alternatives.

Understand that the 'winner' is deemed valuable based on personal opinion, not universal standards.