I sorta went through this with my wife....A customer was trading in an old Trek that would actually fit her (at 4'11") and I scooped it up from the shop. Did a tuneup, checked it out, replaced the bar tape, yada yada. She was excited at the time...excited enough to want to go and tackle clipless pedals. Apparently the pedals we ended up getting her were duds, as one of them was incredibly difficult for her to clip in/clip out and she ended up meeting the pavement once or twice. I've resolved the pedal issue, but she hasn't been on it since. I figure we will try it out again this fall. If she doesn't like it, she doesn't like it and I will sell it and find something suitable for cruising the neighborhood, but she is looking to get into exercising. She did enjoy doing loops around the neighborhood, and did okay when we got out onto a major road.

If your coworkers boyfriend really wants to help her get into road riding, he will have to be patient and try and choose some lightly trafficked roads for awhile. I know when I started I never once imagined I would be riding on some of the roads I currently ride on with no problem

Edit: It was her decision to get the bike, I left it up to her.