I had one sim that I sent on a couple of dates each with the 3 cutest townies in town, LOL. She got equal time with each of them and a roughly equal amount of interaction commands from me. There was one guy she had absolutely no chemistry with even though they got along and spent quality time together. Another guy was the clear winner with the most pink in their relationship bar, so that one became her boyfriend. I've noticed that my sims' friendship and romance bars will fill up at different rates with different sims, so I think it helps to set them up with someone they have a natural attraction to in the first place.