The first time wasn't so bad: "Alcohol played a major part," she told ABCNews.com. "He wasn't expecting anything and neither was I. We talked and that helped set the stage."
"But the next day I was exceedingly sore," she said. "I had shrunk up. It's amazing. I wasn't prepared for it."
The hardest part isn't medical but psychological, say therapists.
"The preparation is kind of scary for a lot of women," said Sandra Ceren, a Del Mar, Calif., psychologist. "Will he see me the way I am now or as I was? Will he see my age spots and sagging breasts. Will he find me as perky?"
One 54-year-old, an author of 13 books on the topic and whose pen name is the Dating Goddess, knows firsthand the pitfalls of getting back in the saddle.
Her husband of 20 years left her at age 48. "I was in fetal position for many months crying," she told ABCNews.com. "I was overweight and who would be attracted to me?"
But since then, she's dated 98 men in four and half years. In her book, "From Fear to Frolic," she recounts getting naked for the first time after her divorce – with 30 to 40 extra pounds.
Her first encounter was with a nearby neighbor who was also overweight. "I felt less self-conscious about the bags and sags."
"The first time is like the first waffle -- you throw it out," she said. "People expect bells and whistles and usually the first time is not like that."
Susan, a therapist from northern California, had been married at 19 for 16 years. A long relationship with someone she met at work ended recently.
"Never in my life have I dated," said the 65-year-old. "I was a single parent raising kids. Every man I ever went out with I met organically."
"I am very, very anxious about being with a stranger – someone I know nothing about," she told ABCNews.com.
She has reason to worry.
According to the Centers for Disease Control, 15 percent of all new HIV cases were among men and women over 50 and seniors are one of the fastest growing groups to contract other sexually transmitted diseases.
"The rules have changed," said Susan Kellogg, director of sex medicine at the Pelvic and Sexual Health Institute of Philadelphia. "They don't grasp condom use or sage sexual behavior."
Women who had been married to high school and college sweethearts may find they have herpes for the first time in their lives, asking Kellogg, "How did this happen? I don't understand."
"Now they are back dating with men who have had more partners in their lifetime and more exposure," she said. "I see women fumbling with this."
But women are also finding fulfillment in these later-in-life relationships.
Alison, a retired interior decorator, had been married for 25 years when the mailman found her husband dead of a heart attack on their western Massachusetts porch.
Their sex life had been "dismal," but when she began dating again, "It was a whole new world -- wow," said the 58-year-old.
"My husband was my first real sexual encounter and I thought, that's how it's supposed be," she told ABCNews.com. "I discovered that wasn't true, and there was nothing wrong with me."
Today, Alison is happily married to a man she met online. There have been health challenges, but, said Alison, "Oh my God, what had I been missing all these years."