While volunteering at the hospital, he met his fiancé Megan McAllister. She was older than him, and they dated for around three years before Markoff proposed to her.
To everyone else, Markoff seemed like an ideal partner. But he had a dark side. He was broke and had accumulated a debt of $130,000 from student loans. He also had a gambling problem that made it even more difficult for him to manage his finances.
Early on in the relationship, Philip Markoff began looking for sexual encounters outside his relationship with his current girlfriend. To remain anonymous, he used different usernames on Craigslist to connect with people seeking sexual activities including transvestites.
On one occasion he also posted an advertisement on Craigslist pretending to be a female masseuse looking for male clients.