Why executives’ control at work can complicate dating

Goldstein said executives often hire matchmakers to save time and energy, which their jobs can consume. Three Day Rule charges from $6,300 to roughly $100,000, depending on the membership, and also offers coaching to help clients improve their dating approach.

The coaching, she said, encourages clients to slow down, be vulnerable and trust the process. That can be difficult for people used to controlling their own destinies. The firm also gathers feedback from both people after dates, using it to help clients understand how potential partners perceive them. Without that input, Goldstein said, people may repeat patterns and wonder why they are not getting a second or third date. The firm’s clients are split roughly evenly between men and women.

Goldstein described a successful entrepreneur whose dates often ended with the women saying they liked him but felt the interaction was more like a friendship. The team could not initially see why the matches were not progressing. Feedback sessions revealed that he was ending every date with a handshake rather than a hug.

The gesture made the dates feel like business transactions, Goldstein said. Changing it made a significant difference, she added, and was something the client might not have noticed without outside feedback. She said that learning about themselves is one of the most valuable parts of matchmaking for clients.