Pretty similar to the initial transformation. Romancable characters (they aren't all, alas) will appear during those days that the tower screws something up and you have the opportunity to take the day off. Date them a few times, and you'll uncover something they may still want.
Most of the time, if you're not locked into an exclusive romance (they'll be marked with a yellow exclusive tag before you commit) YOU will be a valid option for help, which begins to romance. However, you can pair certain versions of your employees together to help each other. For example, Sammy the secretary and JJ (The cowgirl) can pair together.
Ah! Gotcha!
Okay, so for the early characters (Damien, Jolie, and Cassandra), you'll want to chat with them at one of the locations you build (The gym, shakes 'n sundaes, or the computer cafe). Each of the starting characters does appear in two spots, and you'll have more options if you exhaust their conversation in both.
Once you've reached the point where you know what they want, head to R&D and talk to Mason. He'll have a lost of the focis you can make, which you then take back to them in the corresponding location
Let me know if that doesn't do the trick!