Ray, from a mans perspective, looks like he is interested. Whether it was the bosses daughter or a date, there is no commitment right now so why worry. I don't think your friend helped matters. It's OK to be jealous, but don't let him know. Men run from women who are posessive right off the bat. That is the message that your friend is sending. Flirting and hard to get mix works best. Men chase the ones that run away. Just our nature. Just my humble opinion.