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Gain on

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Physical ProximityPlay
Describes decreasing distance, not just physical space but in achievements or goals. SlideShe's gaining on the runner ahead.
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Competitive ProgressPlay
Often used in contexts of competition, highlighting progress against others. SlideOur horse is gaining on the frontrunner.
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Positive ConnotationPlay
Implies a good chance of eventually matching or surpassing the one being gained on. SlideYou're gaining on the chess champion!