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In his experience, they are typically as active as he is with an adventuresome spirit. Sexually zealous and as concerned with physical health and appearance. Middle-aged women (aged 36-49): Does he want to be in a long-term committed relationship? Chief dating women more closely aligned to his age have been similar values and goals. Older women (aged 50-up): Does he want to be Boy Toy or Maintenance Man? Chief saw the advantages of dating an older woman are established and as interested in the fiscal bottom-line.