"If you go to most of these [dating] Web sites, the girls say, 'I'd like to find someone between 25 and 35.' Well, I don't fall into this category anymore," he said. "But when they come and meet me and they go out with me, they say, 'Wait a second, he's 50 years old but he's a whole lot more fun than the 35-year-old man.'"
The Web site works so well for Gil that he said he has to shut his profile down Monday through Friday because of the thousands of e-mail responses he receives.
Entrepreneur and MIT graduate Brandon Wade, a former Microsoft and GE executive, created Seeking Arrangement three years ago. It's an odd business for someone with such a buttoned-up background.
"The inspiration came partially because I was at MIT," he said. "I was very much a nerd and a geek. I wasn't very good at the social scene. I was on regular dating Web sites. I would write messages to beautiful women and I would not hear a response, and I understand why."
Over time, Wade figured out what could allow him to stand apart from the other men on those dating Web sites: His money.
"It would be silly to say, you know, money is not important in society," he said.
Sugar daddies get more than just sex: Many get makeovers, Wade explained. His wife, who he calls a "sugar baby," transformed him into the man he is today.
"I was wearing those Harry Potter glasses and women would not give me any time of day," he said. "But I met my wife, who is 13 years younger than me. She likes to pick stuff out for me. My transformation is one of the benefits that sugar daddies get from a relationship such as this."
Today, nearly 3 million women advertise on this and other sugar daddy dating Web sites. Some ask their sugar daddies for Prada and Gucci bags, fabulous vacations, and even breast implants. Others just ask for help with basics like money for tuition or rent.
Natalie Caplis, a single mother from Montana, was struggling to make ends meet until she made an arrangement that changed her life.
"For me, getting on this site wasn't about getting a $500 pair of shoes or living this lavish lifestyle. It was really about just feeling secure with my basic needs," she explained. "I just, for one time, got to breathe. I got to spend time with my son without having to worry about am I going to have the rent paid?"
One sugar daddy helped her get into a better apartment. He also purchased a brand new car for Caplis and her son to use.
Why are the sugar daddies so willing to give?
"You know how many women need help?" asked Gil. "I'm not giving a handout. I'm getting something. I've seen women there that actually came out of a magazine. The girl who works for me, you can take her out of a magazine."
After meeting one woman through Seeking Arrangement, Gil decided to help her out and hire her as his receptionist. He hired another sugar baby to be his personal "entertainment coordinator" for a month.
As part of their arrangement, Gil told her, "For the next month, you're going to make sure that I have a good life. You make some dinner reservations. We'll go out, we'll roll in the sheets."
Web sites like Seeking Arrangement do offer perks for older, wealthier, and sometimes married men to get into no-strings-attached arrangements with women.
However, this has its share of risks.