Why did Alexander Carter date Claire Howard?

He pursued her as part of a revenge plan against her half-sister Victoria.

How does Alexander pressure Claire to stay silent?

He threatens to cut off the Carter family medical fund paying for her father's treatment.

She Outshines the Stars

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She Outshines the Stars — A woman learns her long-term secret boyfriend dated her only to revenge-target her half-sister.

Claire Howard ends a four-year secret relationship after discovering Alexander Carter used her to retaliate against half-sister Victoria. Victoria exposes Claire's private photos; Alexander blackmails her with her father's treatment fund, forcing Claire to leave San Francisco alone.

Quick answers

Why did Alexander Carter date Claire Howard?: He pursued her as part of a revenge plan against her half-sister Victoria.
How does Alexander pressure Claire to stay silent?: He threatens to cut off the Carter family medical fund paying for her father's treatment.