Sentence:
"There was something ineffably $\qquad$ about Cleopatra's attractive personality that drew many to her - extant coins, bearing the Egyptian queen's visage, however, have led many to believe diminutive that this attribute did not extend to her physiognomy."

Clues:
- "Ineffably $\qquad$ about Cleopatra's attractive personality that drew many to her": Something hard to express ("ineffably") and charming or appealing in her personality.
- The second part suggests that although she had this charming quality, it likely did not extend to her physical appearance ("physiognomy").
- The word "diminutive" in the sentence is likely connected with the coins and her visage meaning small or not impressive physically.

Meaning to Fill:
We want two words describing this appealing personality trait that cannot be easily described.

Option meanings:
- A. attractive - straightforwardly pleasing; fits, but might be redundant since "personality ... that drew many" already implies attractiveness.
- B. diminutive - small, tiny (doesn't fit here because it's about the personality, and the sentence says the coins show the physiognomy was diminutive, not the personality).
- C. overbearing - domineering, unpleasantly assertive (negative; unlikely to be a quality that "drew many").
- D. winsome - charming, appealing, pleasing (good fit for appealing personality).
- E. optimistic - hopeful or positive attitude; not clearly connected to drawing people in or being ineffably appealing.
- F. spirited - lively, full of energy (positive, but might not be described as "ineffably" drawing many).

Conclusion:
The best pair describing an ineffably attractive, charming personality that drew people:
- D. winsome (charming, pleasing)
- A. attractive (directly fits with the idea of drawing many)

Since the question asks for two answers, and "diminutive" is reserved for her visage (the second clause), $\mathbf{B}$ (diminutive) is not a fit here for the blank about personality.

Final answers:
A. attractive
D. winsome