Being someone with money that could invest in things was an easy role to get into. He'd woken up once to see a few of his 'Go bags' show up from home which meant he had more money than he needed to for a place like Indiana. He still went to work regardless because what else was he supposed to do? But he didn't technically need to.
He followed Barbara and fell into 'Dick Grayson, ward of Bruce Wayne' pretty easily despite himself. He let Barbara introduce him and then shook the woman's hand.
There was some flirting which Dick returned easily even if he felt a knot in his chest doing it in front of Barbara. It seemed as if the woman was thrilled to have Barbara here too which Dick suspected was an optics thing - look how inclusive the rich woman was at her party. They chatted up the woman for a bit before she apparently had a 'crisis' to solve in the kitchen.
Once she was far enough away, Dick spoke. "Does Madison really need that many laundry mats?" The woman had been talking about all of the laundry mats she was in the process of opening over the next few months. It was definitely very suspicious.