This should help...
- He'll pick Cloud if you're wearing the Silk Dress, Blonde Wig, and
have the 'best' extra items (the Diamond Tiara, Sexy Cologne, and
Lingerie or Bikini briefs.
- He'll pick Aeris if you're wearing the Silk Dress, the Blonde Wig,
the Lingerie and the Sexy Cologne (in addition to anything else you
may have).
- He'll pick Tifa if you're wearing the Silk Dress, Blonde Wig, and one
or two of the extra items not mentioned above (or anything worse than
that).