Online Dating Isn’t Working. Now What?

Q: I have been a widow for about three years.  (I live with my son, a highly functional autistic man who is independent in most areas but needs my help financially.) I’d love to find a new romantic relationship again, but fear I am destined to be alone. I’ve tried dating sites and have met many men, but we only go out on a date or two and that’s it. Either I don’t feel any connection, which is not very often, or they …

“She Wants to Know Details of My Infidelity”

Q: Last year, I confessed to my wife of 35 years that I’d had affairs with several women approximately 20 years ago. She’s in the process of forgiving me. We have agreed to move forward and have both seen counselors, separately. However, I feel she’s not really moving forward, due to the questions she has about my affairs. She wants me to share my story of infidelity with her: How was I able to do it? How could I do …

Family Ties

Q: How (and when) do I tell a dating partner about my difficult family situation? I haven’t dated in a long time (I’m 59, never married). This is partly due to being a caregiver – first for my dad, who had a stroke, and now my mom, who is recovering from a stroke, and my brother, who has schizophrenia and is in poor physical health. They do live independently, and with some help from community agencies, I don’t have to …

An Unexpected Test

Q: My age is 60. I am very active and energetic and would love to meet the perfect match for me, a partner for life. Dilemma: A few men my age or younger can no longer hold an erection. Thus, the protection of a condom no longer works because it comes off. However, men at this age are taken aback when I suggest that we have blood tests before having intercourse. I have received a lot of shocked looks, comments …

No Long-Term Relationships (Yet)

Q: I am almost 65 years old and have never been married. My longest relationship lasted 10 months, right after I turned 40. Since then, I’ve done some online dating, and like the prospect of finding a partner.  But I’m wondering if it’s possible to find a long-term relationship at this stage of life?  (You should also know that I’ve had five years of therapy that has made a huge difference in my life, and that my two sisters have …

Breaking Up, Boomer Edition

Q: After my wife died three years ago, I reconnected with a woman I’d known in high school. I gave her a ring on Valentine’s Day 2009. Three months later, she died of a massive stroke. That came on the heels of my my father’s death three months earlier. Since then, I have been having extreme bouts of loneliness.  I’m now dating three women, one of whom I especially like. But I’m not sure the feeling is reciprocated. What should I do? I …