I am pleasantly surprised to find that there is different dialog choices when you play each of the genders. I recently finished my first play through as Sara. Now I am going to go through again as Scott. Also he gets a different jacket (YAY!)
I also and letting him flirt with everyone who is an option. Is that going to hurt me in the long run? Is there are point of no return with flirting?
I haven't decided who I want Scott to end up with.
Most of the flirting options lock after their corresponding Loyalty Missions. But there's not really something 'bad' about it. You are not really scolded by anyone nor lose anything. It's not that impacting.