Tough thing with digital is that you have to expose for the highlights. On auto the brighter background is causing the camera's light meter to underexpose (for your subject). In manual you could compensate for this but you'll lose highlight detail.
Best general advice: learn how your camera sees so you aren't relying on it to hopefully see what you see. Buying a hand-held light meter will go a long way towards progressing with your photography.
In this situation a speedlight or on camera flash powered down would've yielded a more even exposure (fill flash). Don't want to use flash: put your subject in the light or let the highlights go and expose for the shaded area.
The second photo, more specifically the subject, can absolutely be pulled in photoshop. Just gotta learn layer masking... best of luck.
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