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I think FOUR is too many interactions, you dilute the focus by having so many characters competing for the same guy, especially if the romance is a subplot. They are too hard for the reader to keep...
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#4: Attribution notice removed
Source: https://writers.stackexchange.com/a/39055 License name: CC BY-SA 3.0 License URL: https://creativecommons.org/licenses/by-sa/3.0/
#3: Attribution notice added
Source: https://writers.stackexchange.com/a/39055 License name: CC BY-SA 3.0 License URL: https://creativecommons.org/licenses/by-sa/3.0/
#2: Initial revision
I think FOUR is too many interactions, you dilute the focus by having so many characters competing for the same guy, especially if the romance is a subplot. They are too hard for the reader to keep track of and remember who is who. I would limit it to three if it were a central plot point, and two as a subplot, since the reader's attention is already distracted by what they need to remember about the main plot. Saying it is "character driven" doesn't alleviate the load; the best character driven stories (in my opinion) devote a lot of attention to a FEW characters, not thin attention to a cast of dozens. Thin attention and deep character development do not go together. And the young uninhibited woman can be both a professional and family rich (I've known at least one such girl) and the colleague could also be single with a son. You can give him things to like about each; the young woman is better in bed, the colleague isn't terrible in bed, but she IS more fun to hang out with and have conversations with, she is more clever, they have a similar sense of humor, and that isn't true with the young woman. He knows because he has been to several professional events with the colleague.