Yes, re-enabling the Two-Timing Dates with a CLEO script, AR-Max code, or savegame editor (if Paul provides an update) is a relatively easy process. I posted some notes on re-enabling the two-timing dates on PS2 in the post linked below. http://www.gtaforums...st&p=1059531776
As noted in the post, the AR-Max codes need a bit of work. They should first check if global $1236 ($1240 on PS2v2) is equal to -1, and if it is, then set it to 0. Otherwise the code will stop the dates from working correctly until it is stopped. For CLEO, something like this untested code should get the job done.
| // re-enables two-timing dates|
$1236 == -1
$1236 = 0
I tried to start a gimp suit date (PC v1 save converted to run on v2 scripts) with Helena but it didn't work - a random date would start, but it never went straight to the kinky-coffee cut-scene. Perhaps there is a glitch in your save. However, the gimp suit date with any girlfriend with this option enabled should not disable two-timing dates.
Enabling the gimp suit or she drives dates for the other girlfriends isn't too difficult using CLEO. It's a bit more problematic using AR-Max codes because they flags are single bits buried in a 4 byte global, and bytes are the smallest unit written by AR-Max. Paul could handle the bits, he managed it with the ped acquaintances, but a girlfriend editor would be a pretty major upgrade. Someone would probably need to provide some incentive.
Added: hmvartak could also make any of these changes. However, his tool it geared more towards repairing glitches, and this doesn't exactly fit in that category. The scripts appear to be working as intended. We may not be happy that the two-timing dates are disabled, but there is nothing to suggest that anything is broken.