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 …

How to Handle the Anti-Cuddler

Q: I’m in my 60s and still want to snuggle up to my wife. She doesn’t want any part of it and says she’s not in the mood. What do you say about this? Dr. Pepper Schwartz: Is she always not in the mood? Or just sometimes? If it’s always, that’s very serious, because the 60s are no time to cut out sex and cuddling altogether. Married people have every right to assume that the pledge to monogamy includes sex …

How to Talk Honestly About Sex Over 50

Q: I’m a 68-year-old widower and have decided to start dating again. I use a vacuum pump to achieve an erection since I have erectile dysfunction caused by long-term diabetes. When do I tell a prospective partner about this? Surprising her with this when things are about to get “hot and heavy” doesn’t seem like a very good idea. My deceased wife was my only partner using this device. She was fine with it, but I have no idea how …

All Is Fair in Love & Gift-Giving?

Q: I remarried two years ago and am happy as can be, except that my husband and I can’t figure out how to deal with gift-giving. I have to buy presents for 10 people on  his side, and he has only one person to buy for on my side. Can you help us find a logical solution? Dr. Pepper Schwartz: Hey, you’re a couple now – split everything! That means you will be doing more for him than he does …

The Online Dating Pitch

Q: I’ve been a widow for almost three years and have gone on some dating sites. I just turned 70, and most of the men in my age category are looking for 50 to 60 year-olds. I don’t look 70, but I don’t look 50 either. I have a difficult time putting things into an email. How and where do I start to email a man I think I may want to meet in person? Dr. Pepper Schwartz: The most …

50 Years Together and Not Even a Hug?

Q: Due to my wife’s health problems, we haven’t had sex in 18 years. Sometimes I think I have forgotten what it would be like to have someone just to hold, sit and talk with. I love my wife very much and would never cheat on her. But it’s not only the sex, I miss just being with someone! She doesn’t let me even hug or kiss her, not even on our 50th wedding anniversary! Dr. Pepper Schwartz: You have …