The Thrills and Challenges of Dating a Younger Man — Be Your Own Brand of Sexy

Samantha’s drive had made her a successful career woman, but her love life had suffered. Her long marriage ended in divorce.

After taking a few years to heal, Samantha decided to dip her toes back into dating. She matched on a dating app with Jacob, an up-and-coming entrepreneur whose startup had just been funded.

Despite the 12-year age gap, they hit it off over their shared interests in tech, entrepreneurship, and a passion for changing the world through innovation. Jacob didn’t seem fazed by Samantha’s power career — in fact, he found her confidence and success incredibly attractive.

As they explored a relationship, problems surfaced. Jacob wanted to have children someday, while Samantha felt that ship had sailed. While Jacob could spend late nights strategizing at his startup’s office, Samantha had to be present at her company, attending events and schmoozing with stakeholders. She sometimes felt Jacob didn’t quite understand the pressures of her role.

Samantha’s many years of life experience sometimes created a gap between them. She felt like she was guiding him through life lessons she had learned long ago, which made her feel disconnected from him.